56816-01-4

Basic information

• Product Name: Ethyl (S)-3-hydroxybutyrate
• Synonyms: (3S)-3-Hydroxybutanoic acid ethyl;(3S)-3-Hydroxybutyric acid ethyl;(S)-3-Hydroxybutanoic acid ethyl;(S)-3-Hydroxybutyric acid ethyl;Ethyl (S)-3-hydroxybutyrate,99%;(S)-(+)-Ethyl 3-Hydrobutyrate;(S)-Ethyl 3-hydroxybutanoate;ETHYL (S)-3-HYDROXYBUTYLATE
• CAS NO: 56816-01-4
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.16
• EINECS: 260-393-1
• Product Categories: Synthetic Organic Chemistry;Chiral Building Blocks;Esters;Organic Building Blocks;Chiral Alcohols;Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds;Chiral Building Blocks;Simple Alcohols (Chiral)
• Mol File: 56816-01-4.mol
• Article Data: 208

Chemical Properties

• Boiling Point: 180-182 °C(lit.)
• Flash Point: 148 °F
• Appearance: Colorless to Yellow/Liquid
• Density: 1.012 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.421(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Soluble in chloroform
• PKA: 14.45±0.20(Predicted)
• BRN: 2347951
• CAS DataBase Reference: Ethyl (S)-3-hydroxybutyrate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl (S)-3-hydroxybutyrate(56816-01-4)
• EPA Substance Registry System: Ethyl (S)-3-hydroxybutyrate(56816-01-4)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 56816-01-4(Hazardous Substances Data)

Usage

Description

Ethyl (S)-3-hydroxybutyrate is a chiral building block for the preparation of bioactive compounds such as pheromones and carbapenem antibiotics.

Chemical Properties

clear colorless liquid

Uses

Different sources of media describe the Uses of 56816-01-4 differently. You can refer to the following data:
1. Ethyl (S)-(+)-3-hydroxybutyrate is used for synthesis of optically active products, used as medical and organic intermediates, an important amino protective agents, pharmaceuticals and synthetic organic makes intermediates, organic synthesis used to introduce t-Boc protect gene.
2. Ethyl (S)-3-Hydroxybutyrate is a product of reductions of keto esters with Baker''s yeast in organic solvents.
3. Ethyl (S)-3-hydroxybutyrate may be used in the preparation of 3-(1′-hydroxyethyl)-2-azetidinones.

Application

Ethyl (S)-3-hydroxybutyrate may be used in the preparation of 3-(1′-hydroxyethyl)-2-azetidinones.

General Description

Ethyl (S)-3-hydroxybutyrate is a chiral building block for the preparation of bioactive compounds such as pheromones and carbapenem antibiotics.

InChI:InChI=1/C6H12O3/c1-3-9-6(8)4-5(2)7/h5,7H,3-4H2,1-2H3

Synthetic route

ethyl acetoacetate (141-97-9) → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With [NEt2H2]-[{RuCl(S)-BINAP}2(μ-Cl)3]; hydrogen In methanol; ethanol at 50℃; under 22801.5 Torr; for 12h; Inert atmosphere; Autoclave; optical yield given as %ee;	100%
With hydrogen In ethanol at 80℃; under 15001.5 Torr; for 10h; enantioselective reaction;	99.5%
With C32H40F6O6P2Pd; hydrogen In acetone at 0℃; under 23272.3 Torr; for 12h; Autoclave; enantioselective reaction;	99%

ethyl 3-hydroxybutyrate (5405-41-4) → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With alcohol dehydrogenase from Lactobacillus kefir; alcohol dehydrogenase from Rhodococcus ruber DSM 44541; YcnD-oxidoreductase at 30℃; for 6h; pH=7.5; aq. buffer; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; enantiospecific reaction;	99%
With Alcaligenes faecalis DSM 13975 cells; alcohol dehydrogenase from Rhodococcus erythropolis; glucose dehydrogenase BS; D-glucose; nicotinamide adenine dinucleotide In alkaline aq. solution at 30℃; for 16h; pH=7.5;

ethyl (3S)-3-{[tert-butyl(dimethyl)silyl]oxy}butanoate (105729-39-3) → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With cerium(III) chloride; sodium iodide In acetonitrile for 3h; Heating;	95%

ethanol (64-17-5) + carbon monoxide (201230-82-2) + (S)-Propylene oxide (16088-62-3) → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With hydrogen; 4-aminopyridine; dicobalt octacarbonyl at 40℃; under 7500.75 Torr; for 24h;	92%
With 1,1-dimethyl-3,3-diethylguanidinecarbonylcobalt at 80℃; under 45004.5 Torr; for 24h; Autoclave;

ethyl (+/-)-3-(3',5'-dinitrobenzoyloxy)butanoate (81378-01-0) → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With titanium(IV) tetraethanolate In ethanol at 78℃; for 96h;	90%

(S)-3-(3',5'-Dinitrobenzoyloxy)-buttersaeureaethylester (79427-05-7) → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran; ethanol	90%
With potassium hydroxide In tetrahydrofuran; ethanol at -5 - 0℃; for 1h;	89%
With potassium hydroxide	79%
With potassium hydroxide In tetrahydrofuran; ethanol at 0℃; for 0.833333h;	113 mg

ethanol (64-17-5) + C10H10N2O7 → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With titanium(IV) isopropylate for 2h; Inert atmosphere; Reflux;	90%

ethanol (64-17-5) + N-(3-hydroxy-butyryl)-benzamide (809275-92-1) → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With erbium(III) triflate at 4℃; for 20h;	89%

ethanol (64-17-5) + (R)-(-)-3-hydroxy-4,4,4-trichlorobutyric β-lactone (16493-63-3) → ethyl (S)-3-hydroxybutyrate (56816-01-4) + ethyl (L)-4-chloro-3-hydroxybutyrate (10488-69-4, 86728-85-0, 87068-18-6, 90866-33-4)

Conditions	Yield
With hydrogen; potassium acetate; palladium on activated charcoal at 25℃; for 80h;	A n/a B 88%

ethyl acetoacetate (141-97-9) → Ethyl (R)-3-hydroxybutanoate (24915-95-5) + ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With citrate-phosphate-borate buffer for 24h; Ambient temperature; baker's yeast immobilized in calcium alginate; Title compound not separated from byproducts;	A n/a B 85%
With Convolvulus sepium for 120h; pH=5.8; aq. phosphate buffer; optical yield given as %ee;	A n/a B 70%
yeast Conversion of starting material; Enzymatic reaction;	A n/a B 26%

ethyl 3-hydroxybutyrate (5405-41-4) + vinyl n-butyrate (123-20-6) → ethyl (S)-3-hydroxybutyrate (56816-01-4) + 3-Butyryloxy-butyric acid ethyl ester

Conditions	Yield
With 4 Angstroem MS; porcin pancreatic lipase In toluene 1.) 37 deg C, 16 h; 2.) 55 deg C, 24 h;	A 83% B n/a
lipase P from Pseudomonas In toluene at 65℃; for 42h;	A 80.5% B n/a

(-)-(R)-Ethyl 3-(mesyloxy)butanoate (126434-58-0) → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With calcium carbonate In water at 80℃; for 3h; Inert atmosphere;	82%
With water; calcium carbonate	70%

ethanol (64-17-5) + (S)-3-Hydroxybutanoic Acid (6168-83-8) → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With sulfuric acid	73%
With sulfuric acid	73%

C6H12O4S → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With hydrogen; Raney-Ni (W4) In ethanol	68%

(S)-3-Hydroxy-dithiobutyric acid methyl ester (107290-90-4) → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With CuCl2-CuO In ethanol for 24h; Ambient temperature;	62%

(2E,4E)-7-(t-Butyl-dimethylsilyloxy)-2,4-octadiensaeuremethylester (79427-02-4) → ethyl (S)-3-hydroxybutyrate (56816-01-4) + (2E,4E)-7-(t-Butyl-dimethylsilyloxy)-2,4-octadiensaeure

Conditions	Yield
With hydrogenchloride In tetrahydrofuran at 30℃; for 3h;	A 58% B 22%

ethanol (64-17-5) + (S)-3-(1-ethoxyethoxy)butyronitrile (77669-83-1) → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With hydrogenchloride; water for 3h;	47%
With hydrogenchloride

3-(Naphthalen-1-ylcarbamoyloxy)-butyric acid ethyl ester (81327-44-8) → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With titanium(IV) tetraethanolate In ethanol at 130℃; under 3800 Torr; for 120h;	45%

ethyl 2-chloro-3-oxo-butyrate (609-15-4) → ethyl (S)-3-hydroxybutyrate (56816-01-4) + ethyl (2R,3S)-2-chloro-3-hydroxybutanoate (110444-43-4)

Conditions	Yield
Baker's yeast;	A n/a B 40%

ethyl 3-hydroxybutyrate (5405-41-4) → (R)-3-hydroxybutyric acid (625-72-9) + ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With sodium hydroxide In water at 30℃; pH=6.9;	A n/a B 36.4%

ethyl acetoacetate (141-97-9) → ethyl (S)-3-hydroxybutyrate (56816-01-4) + 3,3-bismethoxybutyric acid methyl ester (29267-46-7)

Conditions	Yield
With <(-)-2,2'-bis(diphenylphosphino)-3,3'-bibenzothiophene>RuCl2; hydrogen In methanol at 70℃; under 73550.8 Torr; for 2h; Yield given;	A n/a B 5%

ethyl 3-hydroxybutyrate (5405-41-4) → Ethyl (R)-3-hydroxybutanoate (24915-95-5) + ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With pentyl cage-coated capillary column Resolution of racemate;
With homochiral metal-organic cage [Zn3(deprotonated [3+3] macrocyclic Schiff base of trans-1,2-diaminocyclohexane and 4-tert-butyl-2,6-diformylphenol)2] coated capillary column In dichloromethane at 118℃; Resolution of racemate; enantioselective reaction;

ethyl acetoacetate (141-97-9) → (S)-3-Hydroxybutanoic Acid (6168-83-8) + (R)-3-hydroxybutyric acid (625-72-9) + Ethyl (R)-3-hydroxybutanoate (24915-95-5) + ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With Halobacterium halobium; pepton; potassium chloride; water; sodium citrate; magnesium sulfate; sodium chloride at 40℃; for 120h; Irradiation; Yields of byproduct given. Title compound not separated from byproducts;
With Halobacterium halobium; pepton; potassium chloride; sodium citrate; magnesium sulfate; sodium chloride In water at 40℃; for 120h; Irradiation; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

ethyl 3-nitro-oxy-butanoate (100009-46-9) → Ethyl (R)-3-hydroxybutanoate (24915-95-5) + ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(S)-3-Hydroxy-2-methanesulfinyl-butyric acid ethyl ester → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With aluminum amalgam Yield given;
With aluminium amalgam Yield given;

ethyl (3R)-4,4,4-trichloro-3-hydroxybutanoate (166896-25-9) → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With hydrogen; potassium carbonate; palladium on activated charcoal In methanol under 2280 Torr;

ethanol (64-17-5) + (R)-(-)-3-hydroxy-4,4,4-trichlorobutyric β-lactone (16493-63-3) → ethyl (S)-3-hydroxybutyrate (56816-01-4) + ethyl (L)-4-chloro-3-hydroxybutyrate (10488-69-4, 86728-85-0, 87068-18-6, 90866-33-4) + ethyl (R)-3-hydroxy-4,4-dichlorobutyrate

Conditions	Yield
With hydrogen; potassium acetate; palladium on activated charcoal at 25℃; for 80h; Product distribution; other reagents, catalysts, and reaction times;	A 7 % Chromat. B 87 % Chromat. C 6 % Chromat.

ethanol (64-17-5) + poly[(R)-hydroxybutyrate] BIOPOL D300G → ethyl (S)-3-hydroxybutyrate (56816-01-4) + ethyl (S)-3-hydroxyvalerate (54074-85-0, 73143-60-9, 122673-73-8, 73143-67-6) + ethyl (E)-crotonate (623-70-1)

Conditions	Yield
Multistep reaction. Title compound not separated from byproducts;

trans-Crotonaldehyde (123-73-9) + ethanol (64-17-5) → Ethyl (R)-3-hydroxybutanoate (24915-95-5) + ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
Stage #1: trans-Crotonaldehyde; ethanol With dihydrogen peroxide In chloroform at -20℃; for 16h; Stage #2: With N-ethyl-N,N-diisopropylamine In chloroform at 30℃; for 15h; Further stages. Title compound not separated from byproducts.;

Isopropenyl acetate (108-22-5) + ethyl 3-hydroxybutyrate (5405-41-4) → ethyl (S)-3-hydroxybutyrate (56816-01-4) + (R)-3-Acetoxybuttersaeure-ethylester (114592-78-8) + (S)-ethyl 3-acetoxybutanoate

Conditions	Yield
With Candida antarctica lipase B at 23℃; Title compound not separated from byproducts.;

3,4-dihydro-2H-pyran (110-87-2) + ethyl (S)-3-hydroxybutyrate (56816-01-4) → (3S)-3-<<(2R,S)-3,4,5,6-Tetrahydro-2H-pyran-2-yl>oxy>buttersaeure-ethylester (79016-08-3)

Conditions	Yield
	100%
With pyridinium p-toluenesulfonate In dichloromethane for 2.5h; Reflux;	98%
With toluene-4-sulfonic acid In diethyl ether 1.) 0 deg C, 2.5 h, 2.) RT, 0.5 h;	97%

ethyl (S)-3-hydroxybutyrate (56816-01-4) + tert-butyldimethylsilyl chloride (18162-48-6) → ethyl (3S)-3-{[tert-butyl(dimethyl)silyl]oxy}butanoate (105729-39-3)

Conditions	Yield
With 1H-imidazole In dichloromethane at 0 - 23℃;	100%
With 1H-imidazole In dichloromethane at 20℃; for 12h;	100%
With 1H-imidazole In dichloromethane at 0 - 20℃; Inert atmosphere;	98%

ethyl (S)-3-hydroxybutyrate (56816-01-4) + ethyl vinyl ether (109-92-2) → (3S)-3-(1'-Aethoxyaethoxy)buttersaeure-aethylester (82614-86-6)

Conditions	Yield
With trifluoroacetic acid for 48h; Ambient temperature;	98%
With trifluoroacetic acid 1.) a) -5 deg C, 18 h, b) 20 deg C, 2 h;	93%
trifluoroacetic acid 0 deg C, 2 h, then 5 deg C, 16 h;

ethyl (S)-3-hydroxybutyrate (56816-01-4) + ethyl chloromethyl ether (3188-13-4) → (S)-ethyl 3-(ethoxymethoxy)butanoate (137645-28-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 17h; Inert atmosphere;	98%
	90%

ethyl (S)-3-hydroxybutyrate (56816-01-4) + tert-butylchlorodiphenylsilane (58479-61-1) → C22H30O3Si (956225-28-8)

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 18h;	97%

ethyl (S)-3-hydroxybutyrate (56816-01-4) + methanesulfonyl chloride (124-63-0) → (S)-ethyl 3-mesyloxybutyrate (135587-63-2)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 2h;	96.07%
With triethylamine In dichloromethane at 0 - 25℃; for 2h; Inert atmosphere;

ethyl (S)-3-hydroxybutyrate (56816-01-4) → L(+)-3-hydroxy-butyric acid hydrazide (89226-47-1)

Conditions	Yield
With hydrazine hydrate In ethanol; water for 1h; Heating;	94%

ethyl (S)-3-hydroxybutyrate (56816-01-4) + methyl iodide (74-88-4) → ethyl (2S,3S)-3-hydroxy-2-methylbutanoate (78088-28-5)

Conditions	Yield
Stage #1: ethyl (S)-3-hydroxybutyrate With lithium diisopropyl amide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -78 - -40℃; Frater-Seebach alkylation; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -78 - 0℃; for 2h; Frater-Seebach alkylation; Inert atmosphere;	92%
Stage #1: ethyl (S)-3-hydroxybutyrate With lithium diisopropyl amide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -78 - -40℃; Frater-Seebach alkylation; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -78 - 0℃; for 2h; Frater-Seebach alkylation; Inert atmosphere; optical yield given as %de;	92%
Stage #1: ethyl (S)-3-hydroxybutyrate With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - -40℃; for 0.333333h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78 - 0℃; for 3h; Inert atmosphere;	82%

Dimethoxymethane (109-87-5) + ethyl (S)-3-hydroxybutyrate (56816-01-4) → ethyl (3S)-3-(methoxymethoxy)butanoate (73267-69-3)

Conditions	Yield
With iodine; allyl-trimethyl-silane at 20℃; transacetalization;	90%
With iodine; allyl-trimethyl-silane at 20℃;

ethyl (S)-3-hydroxybutyrate (56816-01-4) → (+)-butane-1,3-diol (107-88-0, 6290-03-5, 18826-95-4, 24621-61-2)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 30h; Heating;	89%

ethyl (S)-3-hydroxybutyrate (56816-01-4) + chloromethyl methyl ether (107-30-2) → ethyl (3S)-3-(methoxymethoxy)butanoate (73267-69-3)

Conditions	Yield
With N,N-diethylaniline at 25℃; for 72h;	89%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃;	84%

ethyl (S)-3-hydroxybutyrate (56816-01-4) + 2-[(4-methoxybenzyl)oxy]-3-nitropyridine (350848-02-1) → (S)-3-(4-Methoxy-benzyloxy)-butyric acid ethyl ester (170649-26-0)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.166667h;	89%

ethyl (S)-3-hydroxybutyrate (56816-01-4) + 4-methoxybenzyl-2-pyridylthio carbonate (220235-77-8) → (S)-3-(4-Methoxy-benzyloxy)-butyric acid ethyl ester (170649-26-0)

Conditions	Yield
With silver trifluoromethanesulfonate In dichloromethane for 0.666667h; Ambient temperature;	88%

ethyl (S)-3-hydroxybutyrate (56816-01-4) + O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → (R)-3-(benzyloxy)butanoic acid ethyl ester (112068-33-4)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane; cyclohexane at 20℃; for 1h;	87%
With trifluorormethanesulfonic acid In dichloromethane; cyclohexane for 36h; Ambient temperature;	83%
With trifluorormethanesulfonic acid	78%

acetic acid tert-butyl ester (540-88-5) + ethyl (S)-3-hydroxybutyrate (56816-01-4) → (+)-(5S)-hydroxy-5-oxo-3-hexanoate de tert-butyle (97037-72-4, 125404-66-2, 125404-65-1)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran Claisen condensation;	86%
With lithium diisopropyl amide 1.) THF/hexane, -75 deg C, 20 min, 2.) THF, -50 deg C, 2 h; Yield given. Multistep reaction;

ethyl (S)-3-hydroxybutyrate (56816-01-4) → (2S,1'S)-2-(1-hydroxyethyl)-pent-4-enoate d'ethyle (73574-05-7)

Conditions	Yield
	85.2%

ethyl (S)-3-hydroxybutyrate (56816-01-4) + allyl bromide (106-95-6) → (2S,1'S)-2-(1-hydroxyethyl)-pent-4-enoate d'ethyle (73574-05-7)

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -70℃; Inert atmosphere;	85%
	80%
(i) LDA, THF, (ii) /BRN= 605308/, HMPT; Multistep reaction;

ethyl (S)-3-hydroxybutyrate (56816-01-4) + benzyl bromide (100-39-0) → (R)-3-(benzyloxy)butanoic acid ethyl ester (112068-33-4)

Conditions	Yield
With silver(l) oxide In diethyl ether at 40℃; Inert atmosphere;	85%
With silver(l) oxide In diethyl ether	31%

ethyl (S)-3-hydroxybutyrate (56816-01-4) → 1,3-butanediol (24621-61-2)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 6h;	85%
With lithium aluminium tetrahydride In diethyl ether	82%
With lithium borohydride In methanol; diethyl ether at 20℃; Cooling with ice;	74%
With lithium aluminium tetrahydride In tetrahydrofuran for 2.5h; Ambient temperature;	66%
With lithium aluminium tetrahydride In tetrahydrofuran

ethyl (S)-3-hydroxybutyrate (56816-01-4) + p-toluenesulfonyl chloride (98-59-9) → ethyl (S)-3-tosyloxy-butanoate (100009-40-3)

Conditions	Yield
With pyridine; dmap at 0 - 20℃; for 5.5h;	85%
With pyridine In chloroform	78%
With pyridine In chloroform at 0℃; for 12h;

Upstream product

• 64-17-5 ethanol 
• 16493-63-3 (R)-(-)-3-hydroxy-4,4,4-trichlorobutyric β-lactone 
• 141-97-9 ethyl acetoacetate 
• 5405-41-4 ethyl 3-hydroxybutyrate 
• 79427-05-7 (S)-3-(3',5'-Dinitrobenzoyloxy)-buttersaeureaethylester 
• 81327-44-8 3-(Naphthalen-1-ylcarbamoyloxy)-butyric acid ethyl ester 
• 100009-46-9 ethyl 3-nitro-oxy-butanoate 
• 107290-90-4 (S)-3-Hydroxy-dithiobutyric acid methyl ester 
• 77669-83-1 (S)-3-(1-ethoxyethoxy)butyronitrile 
• 123-20-6 vinyl n-butyrate 
• 112083-27-9 Ethyl (R)-3-hydroxy-4-iodobutanoate 
• 10488-69-4 ethyl (L)-4-chloro-3-hydroxybutyrate 
• 6168-83-8 (S)-3-Hydroxybutanoic Acid 
• 24915-95-5 Ethyl (R)-3-hydroxybutanoate 

Downstream Products

• 73553-29-4 ethyl (2S,3S)-2-benzyl-3-hydroxybutyrate 
• 79427-05-7 (S)-3-(3',5'-Dinitrobenzoyloxy)-buttersaeureaethylester 
• 118988-14-0 (S)-4-ethoxy-4-oxobutan-2-yl benzoate 
• 5405-95-8 4,4'-dimethoxydibenzyl ether 
• 170649-26-0 (S)-3-(4-Methoxy-benzyloxy)-butyric acid ethyl ester 
• 170649-28-2 (3S)-3-<(p-methoxybenzyl)-oxy>-butanal 
• 96735-59-0 (S)-3-((S)-1-Hydroxy-ethyl)-4-((E)-styryl)-azetidin-2-one 
• 100239-17-6 (3S,4S)-3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one 
• 106399-74-0 (3S,4R)-3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one 
• 112068-33-4 (R)-3-(benzyloxy)butanoic acid ethyl ester 
• 107-88-0 (+)-butane-1,3-diol 
• 75492-29-4 (+)-(S)-methyloxetane 
• 6168-83-8 (S)-3-Hydroxybutanoic Acid 
• 16466-61-8 1,2-bis(t-butyloxycarbonyl)hydrazine 

Relevant articles and documents

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Baker's yeast treatment of ethyl 2-chloro-3-oxobutanoate 1, diethyl 2-acetylmalonate 2 and ethyl 2-cyano-3-oxobutanoate 3 was effected in order to obtain enantiomerically enriched compounds.In contrast to the reaction of 2 and 3, efficient diastereo- and enantioselective reduction of 1 provided ethyl 2(R)-chloro-3(S)-hydroxybutanoate.This product was used as precursor of the 1-ethoxycarbonyl-2(S)-hydroxypropyl radical and the diastereoselectivity of the addition of this intermediate to alkenes was studied.

Simple syntheses of (+)-orthosporin and (-)-semivioxanthin methyl ether+

Simple syntheses of (+)-orthosporin(1) and (-)-semivioxanthin methyl ether (11) are described from (S)-ethyl-3-hydroxybutyrate (5) and orsellinic acid derivatives 3 and 4 respectively.

A SIMPLE SYNTHESIS OF (S)-(+)-SULCATOL, THE PHEROMONE OF GNATHOTRICHUS RETUSUS, EMPLOYING BAKER'S YEAST FOR ASYMMETRIC REDUCTION

Ethyl (S)-3-hydroxybutanoate of 87percent optical purity was obtained by the yeast reduction of ethyl acetoacetate and was converted into 85-87percent optically pure (S)-(+)-sulcatol (6-methyl-5-hepten-2-ol) by a 5-step sequence in 73percent overall yield.

The Use of Organic Solvent Systems in the Yeast Mediated Reduction of Ethyl Acetoacetate

The reduction of ethyl acetoacetate to ethyl (S)-3-hydroxybutyrate, mediated by freeze-dried yeast, proceeds in good yield (53-58percent) and with high enantioselectivity (>96percentee) in a number of organic solvents; petroleum ether, diethyl ether, toluene, and carbon tetrachloride.A small amount of water (0.8 ml (g-yeast)-1) is required for the reaction to proceed.The water/yeast/substrate ratio and the solvent polarity have been found to significantly influence the reactivity of the system.The enantiomeric excess was determined by gas chromatography employing a chiral column.

Effect of organic solvents on asymmetric reduction of β-keto esters using cyanobacterium Synechocystis sp. PCC 6803

The asymmetric reduction of tert-butyl 3-oxobutanoate by cyanobacterium Synechocystis sp. PCC 6803 under illumination with red LED light at 25 °C for 24 h afforded the corresponding (R)-β-hydroxy ester in 79% enantiomeric excess (ee) (81% yield), while the addition of toluene (1% (v/v)) to the system gave the corresponding (S)-β-hydroxy ester in >99% ee (87% yield). Organic solvents such as chloroform, benzene, ethylbenzene, cyclohexane, and methylcyclohexane showed similar effects and afforded the corresponding (S)-β-hydroxy ester in >99% ee. However, polar organic solvents, such as DMSO, THF, and ethanol, as well as dodecane—a hydrophobic solvent with a straight long-chain—did not exhibit such effects.

SYNTHESIS OF 3-HYDROXYBUTYRYL 3-HYDROXYBUTYRATE AND RELATED COMPOUNDS

In various embodiments methods of preparing hydroxybutyryl 3-hydroxybutyrate and related compounds are provided along with methods of use thereof.