Methyl (R)-(-)-3-hydroxybutyrate

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Methyl (R)-(-)-3-hydroxybutyrate

  • NameMethyl (R)-(-)-3-hydroxybutyrate
  • CAS3976-69-0
  • Purity99%
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1.What is the Methyl (R)-(-)-3-hydroxybutyrate ?

Methyl (R)-3-hydroxybutyrate may be used in the preparation of (R)-(-)-3-hydroxybutanoic acid and poly-(R)-(-)-3-hydroxybutyrate.

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

(S)-3-hydroxybutyric acid methyl ester
53562-86-0

(S)-3-hydroxybutyric acid methyl ester

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

Conditions
Conditions Yield
With Ru2Cl4-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2*NEt3; hydrogen; In methanol; at 35 ℃; for 48h; under 76000.1 Torr; Title compound not separated from byproducts;
100%
With <((R)-(1,1'-binaphthyl-2,2'-diyl)bis(diphenylphosphine))RuCl2>2NEt3; hydrogen; In methanol; at 35 ℃; for 48h; under 76000.1 Torr; Title compound not separated from byproducts;
100%
With hydrogen; Ru(BICP)Br2; In methanol; at 40 - 65 ℃; under 750.075 - 3750.38 Torr;
95%
With hydrogen; C50H44Cl2N2O8P4Ru(4-)*Zr(4+); In methanol; at 60 ℃; for 20h; under 36201.3 Torr; Product distribution / selectivity;
90%
With ruthenium trichloride; hydrogen; [2R-[1(2'R*,5'R*),2a,5b]]-1,1'-(1,2-phenylene)bis[2,5-dimethylphospholane]; In methanol; at 80 ℃; for 72h; under 37503 Torr; Title compound not separated from byproducts;
85%
at 30 ℃; for 24h; Yields of byproduct given; Kroekera sp No. 2201 (AKU 4705) growning in 10percent glucose solution;
47%
With tartaric acid-Raney Ni-NaBr; hydrogen; In acetic acid; at 100 ℃; for 1h; under 83600 - 98800 Torr; Product distribution; pH=4.0; other modified Raney Ni catalyst system;
With L-glutamic acid; hydrogen; nickel; Product distribution; other reagents (chiral amino acids);
With L-Tartaric acid; ultrasonicated Raney nickel catalyst; hydrogen; acetic acid; sodium bromide; In various solvent(s); at 100 ℃; for 2.5h; Product distribution; other methyl 3-oxoalkanoates; var. times and catalysts;
With L-Tartaric acid; Ni acetylacetonate; zeolite (Si/Al=15); hydrogen; sodium bromide; In tetrahydrofuran; acetic acid; Product distribution; other reagent, enantioselectivity of the reaction;
With hydrogen; (S,S)-tartaric acid modified Raney nickel ((S,S)-TA-NaBr-MRNi-U); Title compound not separated from byproducts;
98 g
With hydrogen; (S,S)-tartaric acid modified Raney nickel ((S,S)-TA-NaBr-MRNi-U); Yield given. Yields of byproduct given;
With potassium hydroxide; Yield given. Multistep reaction. Title compound not separated from byproducts; 1.) EtOH, 25 deg. C, 20 h, 2.) baker's yeast, fermentation medium, 25 deg C, 2 d;
With hydrogen; <(S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl>chloro(p-cymene)ruthenium chloride in poly(dimethylsiloxane) membrane; In various solvent(s); at 60 ℃; for 48h; under 45003.6 Torr; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With (S,S)-SKEWPHOS-RuBr2; hydrogen; In methanol; at 25 ℃; under 7500.6 Torr; Yield given. Yields of byproduct given;
With hydrogen; ultrasonicated (R,R)-tartaric acid-NaBr-modified Raney nickel catalyst <(R,R)-TA-NaBr-MRNi-U>; In various solvent(s); at 100 ℃; for 2.5h; under 750.06 Torr; Title compound not separated from byproducts;
With hydrogen; tartaric acid and NaBr modified Ra-Ni; In acetic acid; at 100 ℃; under 66195.7 Torr; Yield given. Yields of byproduct given;
With hydrogen; L-Tartaric acid; sodium bromide; Yield given. Yields of byproduct given;
With hydrogen; I; In methanol; dichloromethane; at 30 ℃; for 40h; under 64600 Torr; Yield given. Yields of byproduct given;
With L-Tartaric acid; hydrogen; acetic acid; sodium bromide; ultrasonicated Raney nickel catalyst; In various solvent(s); at 100 ℃; for 2.5h; under 73550.8 Torr; Title compound not separated from byproducts;
With hydrogen; tartaric acid-NaBr-modified Raney nickel (TA-NaBr-MRNi); In acetic acid; at 100 ℃; for 5h; under 73550.8 - 88260.9 Torr; Title compound not separated from byproducts;
With Ru<(S)-Ph,Ph-oxoProNOP>(OCOCH3)2; hydrogen; In dichloromethane; at 20 ℃; for 192h; under 108759 Torr; Title compound not separated from byproducts;
With RuCl2<(R)-bis(3-dehydroxy-3-diphenylphosphinoequilenin-4-yl)>(DMF)2; hydrogen; at 100 ℃; for 1h; under 75006 Torr; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With hydrogen; (R,R)-SKEWPHOS-RuBr2; In methanol; at 30 ℃; for 24h; under 7500.6 Torr;
With ammonium sulfate; potassium dihydrogenphosphate; ordinary baker's yeast; magnesium sulfate; Sucrose; for 24h; Title compound not separated from byproducts;
With hydrogen; tartaric acid-NaBr-modified Raney nickel; In tetrahydrofuran; acetic acid; at 60 ℃; under 75006 Torr; Title compound not separated from byproducts;
With hydrogen; ruthenium(II); 1,2-Bis[(S,S)-2,4-dicyclohexylphosphetano]benzene; In methanol; at 80 ℃; for 22h; under 60004.8 Torr; Title compound not separated from byproducts;
With sulfuric acid; hydrogen; [RuCl(benzene)((R)-BIFAPS)]Cl; In water; at 70 ℃; for 2h; under 76000 Torr; Further Variations:; Catalysts; Solvents; Reagents; reaction times; Product distribution;
With ammonium hexafluorophosphate; hydrogen; (R,R)-1,3-Dicyclohexyl-1,3-propanediol cyclic sulfate; dichloro(benzene)ruthenium(II) dimer; In methanol; at 80 ℃; for 20h; under 7500.6 Torr; Title compound not separated from byproducts;
With hydrogen; sodium bromide; nickel; In tetrahydrofuran; at 100 ℃; for 5h; under 67505.4 Torr; Further Variations:; Reagents; Product distribution;
With hydrogen; [RuCl(ν6-benzene)(polyamide chiral ligand)]Cl; In methanol; at 50 ℃; for 14h; under 30002.4 Torr; Further Variations:; Catalysts; Product distribution;
With L-Tartaric acid; hydrogen; sodium bromide; nickel; In tetrahydrofuran; acetic acid; at 60 ℃; for 4h; under 750060 Torr; Further Variations:; Temperatures; Kinetics;
With L-Tartaric acid; hydrogen; sodium bromide; nickel; In tetrahydrofuran; at 100 ℃; for 4h; under 750060 Torr; Title compound not separated from byproducts;
With chiral 1,5-diphenylphosphanylferrocene compound; hydrogen bromide; hydrogen; [Ru(1,5-cyclooctadiene)(C4H7)2]; In methanol; at 50 ℃; for 8h; under 37503 Torr; Further Variations:; Reagents; Temperatures; Product distribution;
With hydrogen; 2,3-dimethyl-1-n-propyl-imidazolium bis(trifluoromethylsulfonyl)imide; Ru[(2,2'-di(PPh2)-6,6'-di(PO3H2)-1,1'-binaphthyl](DMF)2Cl2; In methanol; at 20 ℃; for 22h; under 77572.2 Torr; Further Variations:; Catalysts; Reagents; Product distribution;
With hydrogen bromide; hydrogen; trans-[RuCl2{1,1'-bis[(S,S)-2,4-diiPr-1-phosphetanyl]Fe}Py2]; In methanol; at 50 ℃; under 7500.6 Torr; Title compound not separated from byproducts;
With hydrogen; Zr-Ru-(R)-C44H30P4O6; In methanol; at 60 ℃; for 20h; under 36200.4 Torr; Further Variations:; Catalysts; Temperatures; Pressures; Product distribution;
With hydrogen; [((-)-TMBTP)Ru(p-cymene)I]PF6 on lithiated DOWEX 50WX2 resin; In methanol; Title compound not separated from byproducts;
With chiral dinaphtho[2,1-c;1',2'-e]phosphepine; hydrogen bromide; hydrogen; [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); In methanol; at 100 ℃; for 8h; under 45003.6 Torr; Title compound not separated from byproducts;
With Rhizopus arrhizus culture; In ethanol; at 27 ℃; for 192h; Title compound not separated from byproducts;
With hydrogen; 1-butyl-3-methylimidazolium Tetrafluoroborate; Ru-BINAP; In methanol; at 60 ℃; for 0.0833333h; under 30002.4 Torr; Further Variations:; Solvents; Reagents; Product distribution;
With (Sa)-4-F-C6H4-3H,4H,5H-dinaphtho-[2,1-c;1',2'-e]phosphepine; hydrogen; ruthenium(II) bromide; In methanol; at 120 ℃; for 1h; under 45003.6 Torr; Further Variations:; Reagents; Temperatures; Product distribution; Kinetics;
With hydrogen; acetic acid; L-Tartaric acid; (R,R)-tartaric acid-modified Ni catalyst; In tetrahydrofuran; at 99.85 ℃; under 67505.4 Torr; Further Variations:; Catalysts; Reagents; Product distribution; Kinetics;
With sodium hydroxide; hydrogen; (R,R)-tartaric acid monosodium salt; nickel; In tetrahydrofuran; at 373 ℃; under 75006 Torr; Further Variations:; Reagents; Catalysts; Product distribution;
With hydrogen; mesoporous silica anchored (R)-Ru-BINAP; In methanol; at 20 ℃; for 20h; under 72400.7 Torr; Further Variations:; Catalysts; Product distribution;
With hydrogen; 2-Ph2PferrocenylCH(Me)N(Me)P(3,4-F2Ph)2Ru(II)(PPh3)Cl2; In ethanol; at 20 ℃; for 6h; under 15514.4 Torr; Further Variations:; Catalysts; Solvents; Product distribution;
With hydrogen; sodium bromide; tartaric acid-modified Raney Nickel catalyst; In methanol; at 60 ℃; for 1h; under 45003.6 Torr; pH=4.0; Further Variations:; Solvents; Temperatures; pH-values; Reaction partners; Product distribution;
With hydrogen; acetic acid; L-Tartaric acid; nickel; sodium bromide; at 100 ℃; for 17h; under 33752.7 Torr; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
Product distribution; reductive effect of various yeasts toward β-keto esters discussed;
With hydrogen; acetic acid; L-Tartaric acid; nickel; sodium bromide; at 100 ℃; for 17h; under 33752.7 Torr; Product distribution; various commercial Ni powders/NaBr/(R,R)-tartaric acid;
With hydrogen; RuCl2(DMF)n; In methanol; dichloromethane; at 60 ℃; for 24h; under 38002.6 Torr; Title compound not separated from byproducts.;
With hydrogen; dichloro[(R)-N-diphenylphosphino-N-ethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine](triphenylphosphine)ruthenium; In methanol; at 20 ℃; for 6h; under 16274.9 Torr; Conversion of starting material;
76.2 % ee
With hydrogen; chiral biphosphine-based ruthenium complex; In methanol; at 60 ℃; under 38002.6 Torr; Title compound not separated from byproducts.;
With Hansenula sp; optical yield given as %ee; Enzymatic reaction;
With Aspergillus niger; optical yield given as %ee; Enzymatic reaction;
With hydrogen; In methanol; at 50 ℃; for 24h; under 30003 Torr; optical yield given as %ee; enantioselective reaction; Autoclave;
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; sodium formate; (2S)-N-phenylpyrrolidine-2-carboxamide; In water; at 30 ℃; for 16h; optical yield given as %ee; enantioselective reaction;
With N,N,N,N-triethylhexylammonium hexafluorophosphate; hydrogen; In methanol; at 59.84 ℃; under 37503.8 Torr; optical yield given as %ee;
With hydrogen; In tetrahydrofuran; acetic acid; at 99.84 ℃; for 20h; under 67506.8 Torr; enantioselective reaction; Autoclave;
With L-Tartaric acid; hydrogen; nickel; acetic acid; sodium bromide; In tetrahydrofuran; water; at 99.84 ℃; for 20h; under 67506.8 Torr; pH=3.2; enantioselective reaction; Autoclave;
86 % ee
With hydrogen; In ethanol; at 60 ℃; for 6h; under 30003 Torr; Reagent/catalyst; Overall yield = 15.3 %Chromat.; enantioselective reaction; Catalytic behavior; Inert atmosphere; Autoclave;
80.5% ee
With L-Tartaric acid; hydrogen; nickel; acetic acid; sodium bromide; In tetrahydrofuran; at 99.84 ℃; for 20h; under 67506.8 Torr; pH=4; pH-value; enantioselective reaction;
88 % ee
With hydrogen; acetic acid; In tetrahydrofuran; at 99.84 ℃; for 20h; under 67506.8 Torr; pH=3.2; Temperature; pH-value; Pressure; enantioselective reaction; Autoclave;
89 % ee
With potassium phosphate; Candida parapsilosis aldo-keto reductase CPAR5; NADPH; at 30 ℃; for 8h; pH=6.5; enantioselective reaction; Enzymatic reaction;
78.56 % ee
With potassium phosphate; Candida parapsilosis aldo-keto reductase CPAR6; NADPH; at 30 ℃; for 8h; pH=6.5; enantioselective reaction; Enzymatic reaction;
17.56 % ee
With hydrogen; acetic acid; In tetrahydrofuran; at 110 ℃; for 20h; under 67506.8 Torr; enantioselective reaction; Autoclave;
89 % ee
With dichloro(benzene)ruthenium(II) dimer; hydrogen; In methanol; at 52 ℃; for 2h; under 37503.8 Torr; Reagent/catalyst;
72 % ee
With hydrogen; In tetrahydrofuran; at 59.84 ℃; under 75007.5 Torr; Reagent/catalyst; Overall yield = 100 %; Optical yield = 86 %ee; enantioselective reaction; Autoclave;
With C34H36ClIrNPS2; potassium tert-butylate; hydrogen; In methanol; at 25 - 30 ℃; for 8h; under 7600.51 Torr; Reagent/catalyst; Solvent; Time; enantioselective reaction; Autoclave;
87 % ee
With hydrogen; acetic acid; In tetrahydrofuran; at 59.84 ℃; under 75007.5 Torr; Reagent/catalyst; enantioselective reaction; Autoclave;
86 % ee
With L-Tartaric acid; hydrogen; acetic acid; sodium bromide; In tetrahydrofuran; water; at 99.84 ℃; for 20h; under 67506.8 Torr; Reagent/catalyst; enantioselective reaction; Autoclave;
88 % ee
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C37H35FeN2P; potassium tert-butylate; hydrogen; In methanol; at 20 ℃; for 12h; under 15001.5 Torr; Overall yield = 90 %; enantioselective reaction; Autoclave; Glovebox;
8 % ee
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); 2′-(tert-butylmethylphosphanyl)biphenyl-2-yl camphanate; hydrogen bromide; hydrogen; In methanol; at 80 ℃; for 16h; under 45004.5 Torr; Overall yield = 61.5 %; enantioselective reaction; Autoclave;
45 % ee
With hydrogen; In tetrahydrofuran; at 50 ℃; for 10h; under 30003 Torr; Solvent; Reagent/catalyst; Overall yield = > 99.5 %Chromat.; enantioselective reaction; Catalytic behavior;
84.1 % ee
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (SC,SC,RFC)-1-(diphenylphosphino)-2-[1-N-((4S)-4-tert-butyl-2-oxazolinyl-2-ylmethyl)ethyl]ferrocene; potassium tert-butylate; hydrogen; In methanol; at 20 ℃; for 12h; under 7500.75 Torr; Overall yield = 82 %; Autoclave;
32 % ee
With hydrogen; acetic acid; In tetrahydrofuran; at 59.84 ℃; for 3h; under 75007.5 Torr; Optical yield = 86 %ee; enantioselective reaction; Autoclave;
With dichloro(benzene)ruthenium(II) dimer; (M)-1,1'-bis[(R)-1-(tert-butyldiphenylsiloxy)prop-2-yl]-3,3'-bis(diphenylphosphanyl)-2,2'-biindolyl; hydrogen; In ethanol; at 22 ℃; for 24h; under 3750.38 Torr; Overall yield = 73 %; enantioselective reaction; Autoclave;
86 % ee
With dichloro(benzene)ruthenium(II) dimer; C78H78N2O2P2Si2; hydrogen; In ethanol; at 22 ℃; for 24h; under 3750.38 Torr; Overall yield = 35 %; Autoclave;
82 % ee
With hydrogen; In 1,4-dioxane; Reagent/catalyst; Optical yield = 40 %ee; Autoclave;
With hydrogen; acetic acid; In tetrahydrofuran; water; at 59.84 ℃; for 24h; under 3150.32 Torr; Solvent; Reagent/catalyst; enantioselective reaction; Kinetics; Catalytic behavior; Autoclave;
60 % ee
With hydrogen; In methanol; at 60 ℃; for 22h; under 15001.5 Torr; enantioselective reaction;
4 % ee
With hydrogen; In methanol; at 60 ℃; for 22h; under 15001.5 Torr; enantioselective reaction;
24 % ee
With hydrogen; (Cp)Ru(S-(-)-BINAP)Cl; In methanol; water; at 60 ℃; for 1.5h; under 51714.8 Torr; Product distribution; enantioselective hydrogenation, other acetoaceates;
With C32H39BrMnN2O2P; potassium tert-butylate; hydrogen; In methanol; at 20 ℃; for 16h; under 22502.3 Torr; Optical yield = 30 percent ee; enantioselective reaction; Glovebox; Autoclave;
With D-Glucose; cobalt(II); BaSDR1 reductase; NADH; In aq. phosphate buffer; at 35 ℃; pH=7.5; enantioselective reaction; Kinetics; Enzymatic reaction;
80.8 % ee
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

(S)-3-hydroxybutyric acid methyl ester
53562-86-0

(S)-3-hydroxybutyric acid methyl ester

Methyl (R)-3-hydroxybutyrate
3976-69-0

Methyl (R)-3-hydroxybutyrate

3,3-bismethoxybutyric acid methyl ester
29267-46-7

3,3-bismethoxybutyric acid methyl ester

Conditions
Conditions Yield
With hydrogen; {RuI((R)-2,2'-bis(diphenylphospino)-1,1'-binaphthyl)(p-cymene)}I; In methanol; at 30 ℃; for 35h; under 76000 Torr; Product distribution; other: catalysts, solvents, time, pressure, temperatures;
97%
3%

2.What is the CAS number for Methyl (R)-(-)-3-hydroxybutyrate ?

The CAS number of Methyl (R)-(-)-3-hydroxybutyrate is 3976-69-0.

More information of Methyl (R)-(-)-3-hydroxybutyrate 3976-69-0 are:

CAS?Number

3976-69-0

Density

1.05 g/cm3

Boiling Point

161.9 °C at 760 mmHg

Flash Point

71.7 °C

Vapor Pressure

0.768mmHg at 25°C

Refractive Index

n20/D 1.421(lit.)

HS CODE

29181990

PSA

46.53000

LogP

-0.06970

Pka

13.95±0.20(Predicted)

3.What are another words for Methyl (R)-(-)-3-hydroxybutyrate ?

Synonyms?for?Methyl (R)-(-)-3-hydroxybutyrate 3976-69-0:Methyl (3R)-3-hydroxybutanoate;(R)- (-)-3-Hydroxybutyric acid methyl ester;Methyl (R)-3-Hydroxybutyrate;

4.What is the molecular formula of Methyl (R)-(-)-3-hydroxybutyrate?

The chemical formula of ?Methyl (R)-(-)-3-hydroxybutyrate is?C5H10O3 which containing 5 Carbon atoms,10 Hydrogen atoms and 3 Oxygen atoms,and the molecular weight of??Methyl (R)-(-)-3-hydroxybutyrate?is 118.133.

5.What is Methyl (R)-(-)-3-hydroxybutyrate (3976-69-0) used for?

Methyl (R)-(-)-3-hydroxybutyrate, also known as (R)-3-hydroxybutyric acid methyl ester, is a clear colorless liquid with unique chemical properties. It is an organic compound derived from 3-hydroxybutyric acid and is characterized by its chiral center, which gives it the (R)-configuration. Methyl (R)-(-)-3-hydroxybutyrate is of interest in various fields due to its potential applications and properties.

InChI:InChI=1/C5H10O3/c1-4(6)3-5(7)8-2/h4,6H,3H2,1-2H3/t4-/m1/s1

Relevant articles related to Methyl (R)-(-)-3-hydroxybutyrate:

Article

Source

Ligand-acceleration by a chiral modifier in the enantioselective hydrogenation of methyl acetoacetate on a raney nickel catalyst: Effect of a modifier configuration

Sugimura, Takashi,Nakagawa, Satoshi,Kamata, Naoya,Tei, Takahiro,Tajiri, Takashi,Tsukiyama, Ryo-Ichi,Okuyama, Tadashi,Okamoto, Yasuaki

, p. 271 - 276 (2015)

In situ chiral modification of nickel catalysts for enantioselective hydrogenation of methyl acetoacetate

Bartek, Lukas,Kluson, Petr,Cerveny, Libor

, p. 1642 - 1652 (2005)

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