Methyl (S)-(+)-3-hydroxybutyrate supplier

Name
Methyl (S)-(+)-3-hydroxybutyrate
EINECS 258-628-8
CAS No. 53562-86-0
Article Data160
CAS DataBase
Density 1.05 g/cm³
Solubility Miscible with alcohol. Immiscible with water.
Melting Point
Formula C₅H₁₀O₃
Boiling Point 161.9 °C at 760 mmHg
Molecular Weight 118.133
Flash Point 71.7 °C
Transport Information
Appearance clear colorless liquid
Safety 23-24/25
Risk Codes 38-41
Molecular Structure
Hazard Symbols 38-41:;
Synonyms (+)-(3S)-3-Hydroxybutanoic acid methylester;(3S)-3-Hydroxybutanoic acid methyl ester;(S)-3-Hydroxybutanoic acidmethyl ester;(S)-Methyl3-hydroxybutanoate;Methyl (+)-3-hydroxybutanoate;Methyl (S)-3-hydroxybutyrate;
PSA 46.53000
LogP -0.06970

Synthetic route

: 105-45-3
acetoacetic acid methyl ester

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

Conditions

Conditions	Yield
With cat; hydrogen In methanol; dichloromethane at 25℃; under 77572.2 Torr; for 48h;	100%
With (S)-BiphempRuBr2; hydrogen In methanol at 80℃; under 7600 Torr; for 1h;	100%
With hydrogen; [RuCl2(Sax-4,4'-bis(3-diphenylphosphineestra...)(DMF)]n In methanol at 100℃; under 76000 Torr; for 1h; Catalytic hydrogenation;	100%

: 105-45-3
acetoacetic acid methyl ester

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

B: 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℃; under 76000.1 Torr; for 48h; Title compound not separated from byproducts;	A 100% B n/a
With <((R)-(1,1'-binaphthyl-2,2'-diyl)bis(diphenylphosphine))RuCl2>2NEt3; hydrogen In methanol at 35℃; under 76000.1 Torr; for 48h; Title compound not separated from byproducts;	A n/a B 100%
With hydrogen; Ru(BICP)Br2 In methanol at 40 - 65℃; under 750.075 - 3750.38 Torr;	A n/a B 95%

: 105-45-3
acetoacetic acid methyl ester

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

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

C: 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℃; under 76000 Torr; for 35h; Product distribution; other: catalysts, solvents, time, pressure, temperatures;	A 97% B n/a C 3%

...Expand

: 105-45-3
acetoacetic acid methyl ester

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

B: 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℃; under 76000 Torr; for 35h;	A 97% B 3%
With hydrogen; {RuI((R)-2,2'-bis(diphenylphospino)-1,1'-binaphthyl)(p-cymene)}I In methanol at 30℃; for 35h; Product distribution; in an autoclave; enantioselectivity; other catalysts;	A 96% B 4%
With hydrogen; {RuI((R)-2,2'-bis(diphenylphospino)-1,1'-binaphthyl)(p-cymene)}I In methanol at 30℃; for 35h; in an autoclave;	A 96% B 4%

: 67-56-1
methanol

: 1033766-73-2
perennisaponin E

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

B: 121340-61-2
α-L-Rhamnopyranosyl(1->3)-2β,3β,16α,23-tetrahydroxyolean-12-en-28-saeure-28-O-α-L-rhamnopyranosyl(1->3)-β-D-xylopyranosyl(1->4)-α-L-rhamnopyranosyl(1->2)-β-D-fucopyranosid

Conditions

Conditions	Yield
With sodium methylate at 20℃; for 3h;	A n/a B 92.3%

...Expand

: 67-56-1
methanol

: 1033766-74-3
perennisaponin F

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

B: 121340-61-2
α-L-Rhamnopyranosyl(1->3)-2β,3β,16α,23-tetrahydroxyolean-12-en-28-saeure-28-O-α-L-rhamnopyranosyl(1->3)-β-D-xylopyranosyl(1->4)-α-L-rhamnopyranosyl(1->2)-β-D-fucopyranosid

Conditions

Conditions	Yield
With sodium methylate at 20℃; for 3h;	A n/a B 88.8%

...Expand

: 67-56-1
methanol

: 1033766-71-0
perennisaponin C

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

B: besysaponin C12

Conditions

Conditions	Yield
With sodium methylate at 20℃; for 3h;	A n/a B 88.5%

...Expand

: 67-56-1
methanol

: 1033766-70-9
perennisaponin B

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

B: polygalacic acid 28-O-α-L-rhamnopyranosyl(1->3)-β-D-xylopyranosyl(1->4)-α-L-rhamnopyranosyl(1->2)-β-D-fucopyranoside

Conditions

Conditions	Yield
With sodium methylate at 20℃; for 3h;	A n/a B 88.4%

...Expand

: 67-56-1
methanol

: 1033766-72-1
perennisaponin D

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

B: 121340-61-2
α-L-Rhamnopyranosyl(1->3)-2β,3β,16α,23-tetrahydroxyolean-12-en-28-saeure-28-O-α-L-rhamnopyranosyl(1->3)-β-D-xylopyranosyl(1->4)-α-L-rhamnopyranosyl(1->2)-β-D-fucopyranosid

Conditions

Conditions	Yield
With sodium methylate at 20℃; for 3h;	A n/a B 88.4%

...Expand

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 16088-62-3
(S)-Propylene oxide

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

Conditions

Conditions	Yield
dicobalt octacarbonyl at 20℃; under 760.051 Torr; for 24h;	88%

...Expand

: 133268-19-6
methyl (2R,3S)-2-bromo-3-hydroxy butanoate

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

Conditions

Conditions	Yield
With hydrogen; triethylamine; palladium on activated charcoal In methanol for 4h;	85%

: 142176-65-6
(R)-3-Hydroxy-4-((R)-toluene-4-sulfinyl)-butyric acid methyl ester

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

Conditions

Conditions	Yield
With nickel	81%

: 114607-87-3
Methyl (R)-4-(p-Chlorophenylthio)-3-hydroxybutanoate

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

Conditions

Conditions	Yield
nickel	80%

: 186581-53-3, 908094-01-9
diazomethane

: 6168-83-8
(S)-3-Hydroxybutanoic Acid

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

Conditions

Conditions	Yield
In diethyl ether	12%
With diethyl ether
In diethyl ether Yield given;
In diethyl ether for 0.166667h; Ambient temperature; Yield given;

: 186581-53-3, 908094-01-9
diazomethane

: 153080-60-5
l-menthyl (2R,6S)-6-methyl-4-oxo-2-phenyl-1,3-dioxane-2-carboxylate

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

Conditions

Conditions	Yield
With hydrogenchloride; potassium hydroxide 1.) methanol, 15 min, 3.) ether; Yield given. Multistep reaction;

: 67-56-1
methanol

: 105-45-3
acetoacetic acid methyl ester

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

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

Conditions

Conditions	Yield
With {RuCl((R)-2,2-bis(diphenylphosphino)-1,1'-binaphthyl)(phenyl)}Cl; hydrogen In water at 17℃; under 69873.2 Torr; for 44h;

...Expand

: 1487-49-6
3-hydroxybutyric acid methyl ester

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

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

Conditions

Conditions	Yield
With air; cells of Geotrichum candidum IFO5767 In water at 30℃; for 24h; Product distribution;
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 112℃; Resolution of racemate; enantioselective reaction;

: 114607-75-9
Methyl 4-(4-Chlorophenylthio)-3-oxobutanoate

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Candida guilliermondii 2: 80 percent / Raney nickel View Scheme

: 106353-39-3
Methyl 3-oxo-4-<(R)-p-tolylsulfinyl>butyrate

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / ZnCl2, HAl(iBu)2 / tetrahydrofuran / -78 °C 2: 81 percent / Raney Nickel View Scheme

: 105-45-3
acetoacetic acid methyl ester

(+-)-5-hydroxy-octan-4-one: (+-)-5-hydroxy-octan-4-one

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) LiN(iPr)2 / 1) THF, 0 deg C, 2) THF, -78 deg C, 1 h 2: 60 percent / ZnCl2, HAl(iBu)2 / tetrahydrofuran / -78 °C 3: 81 percent / Raney Nickel View Scheme

: 1201813-85-5
methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-propanoate

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

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

Conditions

Conditions	Yield
With sodium perborate monohydrate In tetrahydrofuran; methanol; water at 20℃; for 12h; Inert atmosphere;
With sodium perborate In tetrahydrofuran; water at 20℃; Inert atmosphere;

: 1190432-98-4
perennisaponin I

: 124-41-4
sodium methylate

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

B: 121340-61-2
α-L-Rhamnopyranosyl(1->3)-2β,3β,16α,23-tetrahydroxyolean-12-en-28-saeure-28-O-α-L-rhamnopyranosyl(1->3)-β-D-xylopyranosyl(1->4)-α-L-rhamnopyranosyl(1->2)-β-D-fucopyranosid

Conditions

Conditions	Yield
In methanol at 20℃; for 3h;	A n/a B 1.5 mg

...Expand

: 1190433-12-5
perennisaponin J

: 124-41-4
sodium methylate

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

B: 121340-61-2
α-L-Rhamnopyranosyl(1->3)-2β,3β,16α,23-tetrahydroxyolean-12-en-28-saeure-28-O-α-L-rhamnopyranosyl(1->3)-β-D-xylopyranosyl(1->4)-α-L-rhamnopyranosyl(1->2)-β-D-fucopyranosid

Conditions

Conditions	Yield
In methanol at 20℃; for 3h;	A n/a B 1.5 mg

...Expand

: 1190433-29-4
perennisaponin K

: 124-41-4
sodium methylate

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

B: 121340-61-2
α-L-Rhamnopyranosyl(1->3)-2β,3β,16α,23-tetrahydroxyolean-12-en-28-saeure-28-O-α-L-rhamnopyranosyl(1->3)-β-D-xylopyranosyl(1->4)-α-L-rhamnopyranosyl(1->2)-β-D-fucopyranosid

Conditions

Conditions	Yield
In methanol at 20℃; for 3h;	A n/a B 1.5 mg

...Expand

: 1190433-46-5
perennisaponin L

: 124-41-4
sodium methylate

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

B: 121340-61-2
α-L-Rhamnopyranosyl(1->3)-2β,3β,16α,23-tetrahydroxyolean-12-en-28-saeure-28-O-α-L-rhamnopyranosyl(1->3)-β-D-xylopyranosyl(1->4)-α-L-rhamnopyranosyl(1->2)-β-D-fucopyranosid

Conditions

Conditions	Yield
In methanol at 20℃; for 3h;	A n/a B 1.5 mg

...Expand

: 1190433-62-5
perennisaponin M

: 124-41-4
sodium methylate

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

B: 121340-61-2
α-L-Rhamnopyranosyl(1->3)-2β,3β,16α,23-tetrahydroxyolean-12-en-28-saeure-28-O-α-L-rhamnopyranosyl(1->3)-β-D-xylopyranosyl(1->4)-α-L-rhamnopyranosyl(1->2)-β-D-fucopyranosid

Conditions

Conditions	Yield
In methanol at 20℃; for 3h;	A n/a B 1.5 mg

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 300-85-6, 625-71-8
3-Hydroxybutyric acid

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

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

Conditions

Conditions	Yield
In diethyl ether; water; ethyl acetate for 0.25h;

...Expand

: 623-43-8, 4358-59-2, 18707-60-3, 130981-57-6
methyl crotonate

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: bis[2-(diphenylphosphino)phenyl] ether; copper(l) chloride; sodium t-butanolate / tetrahydrofuran; methanol 2: Candida antarctica lipase immobilized on acrylic resin / hexane / 24 h / 70 °C / Sealed tube; Enzymatic reaction 3: sodium perborate tetrahydrate / tetrahydrofuran; water / 1 h / 20 °C View Scheme

: 1185248-82-1
(S)-methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate

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

Conditions

Conditions	Yield
With sodium perborate tetrahydrate In tetrahydrofuran; water at 20℃; for 1h;

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

: 18162-48-6
tert-butyldimethylsilyl chloride

: 148555-62-8
(3S)-3-(tert-butyldimethylsilyloxy)butanoic acid methyl ester

Conditions

Conditions	Yield
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 0 - 20℃; for 3h; Inert atmosphere;	100%
With 1H-imidazole In N,N-dimethyl-formamide at 70℃; for 8h;	99%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	98%

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

: 58479-61-1
tert-butylchlorodiphenylsilane

: 215444-96-5
methyl (3S)-3-{[tert-butyl(diphenyl)silyl]oxy}butanoate

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide	100%
With 1H-imidazole In N,N-dimethyl-formamide at 53℃; for 18h;	100%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃;	99%

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

: 124-63-0
methanesulfonyl chloride

: (S)-3-Methanesulfonyloxy-butyric acid methyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0℃;	99%
With triethylamine In dichloromethane for 1h; Ambient temperature;	91%

: 110-87-2
3,4-dihydro-2H-pyran

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

: (S)-3-(Tetrahydro-pyran-2-yloxy)-butyric acid methyl ester

Conditions

Conditions	Yield
With hydrogen cation	97%

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

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 350848-03-2
methyl (S)-3-(4-methoxybenzyloxy)butanoate

Conditions

Conditions	Yield
With 10-camphorsulfonic acid In dichloromethane at 20℃; for 7h;	95%
With D,L-camphorsulfonic acid In dichloromethane at 20℃; for 12h; Inert atmosphere;	70%
With camphor-10-sulfonic acid In dichloromethane

: 540-88-5
acetic acid tert-butyl ester

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

: 97037-72-4, 125404-66-2, 125404-65-1
(+)-(5S)-hydroxy-5-oxo-3-hexanoate de tert-butyle

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78 - -15℃;	94%
Stage #1: acetic acid tert-butyl ester With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: (S)-3-hydroxybutyric acid methyl ester In tetrahydrofuran at -50 - -15℃; Claisen condensation;	93%
Stage #1: acetic acid tert-butyl ester With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: (S)-3-hydroxybutyric acid methyl ester In tetrahydrofuran at -50℃; for 2h;	87%
With lithium diisopropyl amide
With lithium diisopropyl amide In tetrahydrofuran

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

: 24621-61-2
1,3-butanediol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 1h; Ambient temperature;	91%
With hydrogen; Nishimura catalyst <(45.9% Rh/19.9% Pt) oxide> In methanol at 25℃; under 75007.5 Torr;
With lithium borohydride

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

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 90124-15-5
(S)-3-(benzyloxy)butanoic acid methyl ester

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 24h;	89%
With trifluorormethanesulfonic acid In hexane; dichloromethane at 0℃;
With trifluorormethanesulfonic acid In hexane; dichloromethane for 4h; Ambient temperature;
With cyclohexane In dichloromethane; trifluorormethanesulfonic acid

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

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 474825-97-3
(S)-3-hydroxy-N-methoxy-N-methylbutanamide

Conditions

Conditions	Yield
With isopropylmagnesium chloride In tetrahydrofuran at -30 - 0℃; for 3.5h;	89%

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

: 358-23-6
trifluoromethylsulfonic anhydride

: 112424-25-6
(S)-3-(Trifluormethylsulfonyloxy)buttersaeure-methylester

Conditions

Conditions	Yield
With pyridine In dichloromethane at 40℃; for 2h;	87%

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

: 20445-33-4, 39637-99-5
(R)-methoxytrifluoromethylphenylacetyl chloride

: methyl (3S)-3-<(S)-(-)-α-methoxy-α-(trifluoromethyl)phenylacetyl>butyrate

Conditions

Conditions	Yield
With pyridine In tetrachloromethane for 12h; Ambient temperature;	86%

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

: 870-63-3
prenyl bromide

: (S)-methyl 2-((S)-1-hydroxyethyl)-5-methylhex-4-enoate

Conditions

Conditions	Yield
Stage #1: (S)-3-hydroxybutyric acid methyl ester With lithium diisopropyl amide In tetrahydrofuran at -30℃; for 1.75h; Stage #2: prenyl bromide In tetrahydrofuran; 1,2-dimethoxyethane at -78 - -60℃; for 2.75h;	86%
Stage #1: (S)-3-hydroxybutyric acid methyl ester With lithium diisopropyl amide In tetrahydrofuran at -30℃; for 1.75h; Stage #2: prenyl bromide In tetrahydrofuran; 1,2-dimethoxyethane at -78 - 60℃; for 2.5h;	86%
Stage #1: (S)-3-hydroxybutyric acid methyl ester With lithium diisopropyl amide In tetrahydrofuran at -78 - -30℃; for 1.75h; Stage #2: prenyl bromide In tetrahydrofuran; 1,2-dimethoxyethane at -60℃; for 2.75h;	86%
Stage #1: (S)-3-hydroxybutyric acid methyl ester With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -50 - -30℃; for 1.75h; Stage #2: prenyl bromide In tetrahydrofuran; 1,2-dimethoxyethane; hexane at -78 - 20℃; for 2.75h;	86%
Stage #1: (S)-3-hydroxybutyric acid methyl ester With lithium diisopropyl amide In tetrahydrofuran at -70℃; for 1h; Inert atmosphere; Stage #2: prenyl bromide With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at -70 - -10℃; for 3h; Inert atmosphere; diastereoselective reaction;	81%

: 3756-30-7
1-iodo-2-methyl-2-propene

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

: 123408-35-5
(2S,1'S)-2-(1-hydroxyethyl)-pent-4-enoate methyle

Conditions

Conditions	Yield
	80%

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

: 74-88-4
methyl iodide

: 66767-60-0
methyl (2S,3S)-3-hydroxy-2-methylbutanoate

Conditions

Conditions	Yield
Stage #1: (S)-3-hydroxybutyric acid methyl ester With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: methyl iodide at -78℃; for 1.5h;	79%
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide In tetrahydrofuran at -78℃;	78%
Stage #1: (S)-3-hydroxybutyric acid methyl ester With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere;	77%

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

: 294198-49-5
(4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoic acid

: 473555-54-3
methyl (3S,8R,9S)-8-benzyloxy-9-tert-butyldimethylsiloxy-3-methyl-5-oxo-4-oxadeca (6E)-enoate

Conditions

Conditions	Yield
With dmap; (1S)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h; Keck condensation;	75%

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

: 1270043-91-8
dimethyl (2S,2E)-2-((3-(4-hydroxy-3,5-dimethoxyphenyl)acryloyl)oxy)succinate

: C22H34O7Si

Conditions

Conditions	Yield
With dmap In dichloromethane at 20℃;	73.7%

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

: 98-59-9
p-toluenesulfonyl chloride

: 91366-13-1
(3S)-methyl 3-(p-toluenesulfonyl)butyrate

Conditions

Conditions	Yield
In pyridine at -5 - 0℃; for 48h;	70%
With pyridine Ambient temperature;
With pyridine; triethylamine In toluene at 0 - 20℃; Inert atmosphere;

Methyl (S)-(+)-3-hydroxybutyrate Specification

The IUPAC name of Methyl (S)-(+)-3-hydroxybutyrate is methyl (3S)-3-hydroxybutanoate. With the CAS registry number 53562-86-0, it is also named as Butanoic acid, 3-hydroxy-, methyl ester, (S)-. The product's categories are Alcohols, Hydroxy Esters and Derivatives; Chiral Compounds; Building Blocks for Liquid Crystals; Chiral Building Blocks; Chiral Compounds (Building Blocks for Liquid Crystals); Functional Materials; Simple Alcohols (Chiral); Synthetic Organic Chemistry; Chiral Building Blocks; Esters; Organic Building Blocks. It is clear colorless liquid which should be sealed in the container and stored at the temperature of 0-6°C.

The other characteristics of Methyl (S)-(+)-3-hydroxybutyrate can be summarized as: (1)ACD/LogP: -0.55; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 3; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 4; (6)Polar Surface Area: 35.53 Å²; (7)Index of Refraction: 1.42; (8)Molar Refractivity: 28.48 cm³; (9)Molar Volume: 112.4 cm³; (10)Polarizability: 11.29×10^-24 cm³; (11)Surface Tension: 33.2 dyne/cm; (12)Flash Point: 71.7 °C; (13)Enthalpy of Vaporization: 46.4 kJ/mol; (14)Boiling Point: 161.9 °C at 760 mmHg; (15)Vapour Pressure: 0.768 mmHg at 25°C; (16)Rotatable Bond Count: 3; (17)Exact Mass: 118.062994; (18)MonoIsotopic Mass: 118.062994; (19)Topological Polar Surface Area: 46.5; (20)Heavy Atom Count: 8; (21)Complexity: 79.7; (22)Defined Atom StereoCenter Count: 1.

When you are using this chemical, please be cautious about it as the following:
It is irritating to skin and has risk of serious damage to the eyes. So people should not breathe vapour and avoid contact with skin and eyes.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(OC)C[C@@H](O)C
2. InChI:InChI=1/C5H10O3/c1-4(6)3-5(7)8-2/h4,6H,3H2,1-2H3/t4-/m0/s1
3. InChIKey:LDLDJEAVRNAEBW-BYPYZUCNBL
4. Std. InChI:InChI=1S/C5H10O3/c1-4(6)3-5(7)8-2/h4,6H,3H2,1-2H3/t4-/m0/s1
5. Std. InChIKey:LDLDJEAVRNAEBW-BYPYZUCNSA-N

Product Name

Methyl (S)-(+)-3-hydroxybutyrate

Synthetic route

Methyl (S)-(+)-3-hydroxybutyrate Specification

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