60456-26-0

Basic information

• Product Name: (R)-Glycidyl butyrate
• Synonyms: (R)-Glycidyl butyrat;(R)-Glycidyl butyrate, 92-94% 10GR;(R)-Oxiran-2-ylMethyl butyrate;Butanoic acid, (2R)-oxiranylMethyl ester;Butanoic acid, oxiranylMethyl ester, (R)-;(R)-(-)-Glycidyl butyrate, (R)-(-)-Glycidyl butanoate;(2R)-2-Oxiranylmethyl Ester Butanoic Acid;(R) - glycidyl ester of butyric acid
• CAS NO: 60456-26-0
• Molecular Formula: C₇H₁₂O₃
• Molecular Weight: 144.17
• EINECS: -0
• Product Categories: Ring Systems;Small molecule;chiral;API intermediates;CHIRAL COMPOUNDS;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Oxiranes;Simple 3-Membered Ring Compounds;Synthetic Organic Chemistry;Chiral Compound;Esters
• Mol File: 60456-26-0.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 197 °C(lit.)
• Flash Point: 185 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.032 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.402mmHg at 25°C
• Refractive Index: n20/D 1.428(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Ethyl Acetate
• Water Solubility: insoluble
• BRN: 5246881
• CAS DataBase Reference: (R)-Glycidyl butyrate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Glycidyl butyrate(60456-26-0)
• EPA Substance Registry System: (R)-Glycidyl butyrate(60456-26-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-42/43
• Safety Statements: 23-36/37-45-36/37/39-26
• RIDADR: 2810
• WGK Germany: 3
• F: 10-21
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 60456-26-0(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

Different sources of media describe the Uses of 60456-26-0 differently. You can refer to the following data:
1. (R)-Glycidyl butyrate is a reagent used in the synthesis of glycidol, a stabilizer in manufacturing of vinyl polymers; intermediate in synthesis of glycerol, glycidyl ethers, and amines; additive for oil and synthetic hydraul ic fluids; epoxy resin diluent.
2. (2R)-2-Oxiranylmethyl Ester Butanoic Acid is a reagent used in the synthesis of glycidol, a stabilizer in manufacturing of vinyl polymers; intermediate in synthesis of glycerol, glycidyl ethers, and amines; additive for oil and synthetic hydraulic fluids; epoxy resin diluent.

InChI:InChI=1/C7H12O3/c1-2-3-7(8)10-5-6-4-9-6/h6H,2-5H2,1H3/t6-/m0/s1

Synthetic route

butyric acid-3-chloro-(S)-2-hydroxy-propyl ester (890051-54-4) → (R)-glycidyl butyrate (60456-26-0)

Conditions	Yield
With sodium hydroxide for 12h; Reflux;	90%
With potassium phosphate; [(S,S)-(salen)Co(II)]2*Al(NO3)3 In various solvent(s) at 20℃;	40%
With potassium tert-butylate In 1,2-dichloro-ethane at 0℃; for 1h;	72.0 %Chromat.

butyryl chloride (141-75-3) + (S)-oxiranemethanol (60456-23-7) → (R)-glycidyl butyrate (60456-26-0)

Conditions	Yield
With calcium oxide In 2-methyltetrahydrofuran at 20℃; for 6h; Green chemistry; chemoselective reaction;	89%

(+/-)-glycidyl butyrate (2461-40-7) → 1-sn-monobutyroylglycerol (5309-42-2) + (R)-glycidyl butyrate (60456-26-0) + (S)-2,3-dihydroxypropyl butyrate (126254-87-3)

Conditions	Yield
With [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II); air; acetic acid In tetrahydrofuran at 0 - 20℃;	A n/a B 46% C n/a

(+/-)-glycidyl butyrate (2461-40-7) → (R)-glycidyl butyrate (60456-26-0) + (S)-2,3-dihydroxypropyl butyrate (126254-87-3)

Conditions	Yield
With [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II); air; acetic acid In tetrahydrofuran at 0 - 20℃;	A 46% B n/a

(+/-)-glycidyl butyrate (2461-40-7) → (R)-glycidyl butyrate (60456-26-0) + (R)-oxiranemethanol (57044-25-4)

Conditions	Yield
With sodium phosphate buffer; 25 kDa lipase-like enzyme immobilized on DEAE-Sepharose In 1,4-dioxane; water at 25℃; for 10h; pH=7.00;	A n/a B 45%
With thermomyces lanuginosa In 1,4-dioxane; aq. phosphate buffer at 30℃; for 2h; pH=7; Temperature; Resolution of racemate; Enzymatic reaction;	A n/a B n/a

(+/-)-glycidyl butyrate (2461-40-7) → butyric acid-3-chloro-(S)-2-hydroxy-propyl ester (890051-54-4) + butyric acid-3-chloro-(R)-2-hydroxy-propyl ester (890051-57-7) + (R)-glycidyl butyrate (60456-26-0) + (S)-glycidyl butyrate (65031-96-1)

Conditions	Yield
With hydrogenchloride; (R,R)-[Co(salen)]2*GaCl3 In diethyl ether at 0 - 4℃; for 4h;	A 45% B n/a C n/a D 43%

(+/-)-glycidyl butyrate (2461-40-7) → (R)-glycidyl butyrate (60456-26-0) + (S)-2,3-dihydroxypropyl butyrate (126254-87-3) + (S)-glycidyl butyrate (65031-96-1)

Conditions	Yield
With (acetao)(aqua)(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene-1,2-cyclohexanediamino)-cobalt(III); water In tetrahydrofuran at 0℃; for 12h; Jacobsen rearrangement; optical yield given as %ee;	A 40% B n/a C n/a

(+/-)-glycidyl butyrate (2461-40-7) → (R)-glycidyl butyrate (60456-26-0) + (R)-oxiranemethanol (57044-25-4) + (S)-oxiranemethanol (60456-23-7)

Conditions	Yield
With Rhizopus oryzae lipase on dextran sulfate coated Sepabeads In water at 25℃; pH=7; Enzymatic reaction; Title compound not separated from byproducts;

butanoic acid anhydride (106-31-0) + (S)-oxiranemethanol (60456-23-7) → (R)-glycidyl butyrate (60456-26-0)

Conditions	Yield
With triethylamine; dmap In dichloromethane at 0 - 20℃; for 1h; Product distribution / selectivity;	n/a

vinyl n-butyrate (123-20-6) + (S)-oxiranemethanol (60456-23-7) → (R)-glycidyl butyrate (60456-26-0)

Conditions	Yield
With Rhizopus oryzae lipase/polystyrene fibers at 35℃; for 1h; Kinetics;

(+/-)-glycidyl butyrate (2461-40-7) → 1-sn-monobutyroylglycerol (5309-42-2) + (R)-glycidyl butyrate (60456-26-0) + (S)-glycidyl butyrate (65031-96-1)

Conditions	Yield
With 4CF3O3S(1-)*Co(3+)*Y(3+)*C36H52N2O2(2-); water In neat (no solvent) at 20℃; for 12h; Overall yield = 19 %; enantioselective reaction;	A n/a B n/a C n/a

4-(methylthio)phenyl isocyanate (1632-84-4) + (R)-glycidyl butyrate (60456-26-0) → (R)-<3-<4-(methylthio)phenyl>-2-oxo-5-oxazolidinyl>methyl butyrate (121373-23-7)

Conditions	Yield
With Tributylphosphine oxide; lithium bromide In xylene for 2h; Heating;	100%

(R)-glycidyl butyrate (60456-26-0) + 2,6-diaminopurine (1904-98-9) → Butyric acid (R)-3-(2,6-diamino-purin-9-yl)-2-hydroxy-propyl ester

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 4h;	100%

(R)-glycidyl butyrate (60456-26-0) + 4-(2-fluoro-4-isothiocyanato-phenyl)-morpholine → (R)-3-(3-Fluoro-4-morpholin-4-yl-phenyl)-5-hydroxymethyl-oxazolidine-2-thione (760983-13-9)

Conditions	Yield
Stage #1: (R)-glycidyl butyrate; 4-(2-fluoro-4-isothiocyanato-phenyl)-morpholine With Triphenylphosphine oxide; lithium bromide In xylene at 110 - 115℃; for 1h; Stage #2: With sodium methylate In methanol at 26 - 28℃; for 2h; Further stages.;	100%

carbon monoxide (201230-82-2) + (R)-glycidyl butyrate (60456-26-0) → (R)-4-(butyroxymethyl)-2-propiolactone

Conditions	Yield
With chromium(III) octaethylporphyrinato tetracarbonylcobaltate at 40℃; under 46543.3 Torr; for 6h;	100%

benzyl (5-iodopyridin-2-yl)carbamate + (R)-glycidyl butyrate (60456-26-0) → (R)-5-(hydroxymethyl)-3-(5-iodopyridin-2-yl)oxazolidin-2-one

Conditions	Yield
Stage #1: benzyl (5-iodopyridin-2-yl)carbamate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.33333h; Inert atmosphere; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;	99%

benzyl (3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)carbamate + (R)-glycidyl butyrate (60456-26-0) → (R)-3-(3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)-5-(hydroxymethyl)oxazolidin-2-one

Conditions	Yield
Stage #1: benzyl (3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)carbamate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.33333h; Inert atmosphere; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;	98%

2-[4-[[(benzyloxy)carbonyl]amino]-2-fluorophenyl]-hexahydro-1H-spiro[cyclopenta[c]pyrrole-5,2'-[1,3]dioxolane] (1395322-89-0) + (R)-glycidyl butyrate (60456-26-0) → (5R)-3-(3-fluoro-4-(tetrahydro-1H-spiro[cyclopenta[c]pyrrole-5,2'-[1,3]dioxolane]-2(3H)-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one (1395322-90-3)

Conditions	Yield
Stage #1: 2-[4-[[(benzyloxy)carbonyl]amino]-2-fluorophenyl]-hexahydro-1H-spiro[cyclopenta[c]pyrrole-5,2'-[1,3]dioxolane] With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran at -78 - 20℃; for 12.5h; Stage #3: With water; ammonium chloride In tetrahydrofuran	97%

1-(4-benzyloxycarbonylamino-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (1259556-26-7) + (R)-glycidyl butyrate (60456-26-0) → 1-[(4-(5R)-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

Conditions	Yield
Stage #1: 1-(4-benzyloxycarbonylamino-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃; Stage #3: With ammonium chloride In tetrahydrofuran; hexane	96%

1-(4-benzyloxycarbonylamino-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (1259556-26-7) + (R)-glycidyl butyrate (60456-26-0) → 1-[4-((5R)-hydroxymethyl-2-oxooxazolidin-3-yl)phenyl]-3-azabicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (1259556-27-8)

Conditions	Yield
Stage #1: 1-(4-benzyloxycarbonylamino-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃;	96%

N-phenyl methyl carbamate (2603-10-3) + (R)-glycidyl butyrate (60456-26-0) → (R)-5-(hydroxymethyl)-3-phenyl-2-oxooxazolidine (87508-42-7)

Conditions	Yield
Stage #1: N-phenyl methyl carbamate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.63333h; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃; for 22.1h;	95%

benzyl (4-((tert-butyldimethylsilyl)oxy)-3-fluorophenyl)carbamate + (R)-glycidyl butyrate (60456-26-0) → C16H24FNO4Si

Conditions	Yield
Stage #1: benzyl (4-((tert-butyldimethylsilyl)oxy)-3-fluorophenyl)carbamate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.33333h; Inert atmosphere; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;	94%

5-(4-benzyloxycarbonylamino-2-fluorophenyl)[1,2,5]triazepane-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester (1443005-33-1) + (R)-glycidyl butyrate (60456-26-0) → 5(R)-(hydroxymethyl)-3-(3-fluoro-4-(1-(benzyloxycarbonyl)-2-(tert-butoxycarbonyl)[1,2,5]triazepan-5-yl)phenyl)oxazolidin-2-one (952150-17-3)

Conditions	Yield
Stage #1: 5-(4-benzyloxycarbonylamino-2-fluorophenyl)[1,2,5]triazepane-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Inert atmosphere; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃; for 23.1667h; Inert atmosphere;	93%

(R)-glycidyl butyrate (60456-26-0) + [4-(5,7-dihydro-pyrrolo[3,4-b]pyridin-6-yl)-3-fluoro-phenyl]-carbamic acid benzyl ester (344460-43-1) → (5R)-3-[4-(5,7-Dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-3-fluorophenyl]-5-(hydroxymethyl)-2-oxazolidinone (344459-52-5)

Conditions	Yield
Stage #1: [4-(5,7-dihydro-pyrrolo[3,4-b]pyridin-6-yl)-3-fluoro-phenyl]-carbamic acid benzyl ester With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran at -78 - 20℃;	92%
Stage #1: [4-(5,7-dihydro-pyrrolo[3,4-b]pyridin-6-yl)-3-fluoro-phenyl]-carbamic acid benzyl ester With n-butyllithium In tetrahydrofuran Stage #2: (R)-glycidyl butyrate In tetrahydrofuran at -78 - 20℃;

(R)-glycidyl butyrate (60456-26-0) + (5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-carbamic acid benzyl ester (164149-25-1) → (R)-5-hydroxymethyl-3-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-oxazolidin-2-one (741721-20-0)

Conditions	Yield
Stage #1: (5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-carbamic acid benzyl ester With lithium hexamethyldisilazane In tetrahydrofuran at -70℃; for 1h; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran at -70 - 20℃;	92%

(R)-glycidyl butyrate (60456-26-0) + N-benzyloxycarbonyl-3-fluoro-4-(4-phenylpiperazinyl)aniline (556801-41-3) → (R)-[N-3-(3'-fluoro-4'-(4"-phenylpiperazinyl)phenyl)-2-oxo-5-oxazolidinyl]methanol (465520-07-4)

Conditions	Yield
With lithium aluminium tetrahydride; n-butyllithium In tetrahydrofuran; hexane at -61 - 95℃; for 1h; Inert atmosphere;	90.86%
Stage #1: N-benzyloxycarbonyl-3-fluoro-4-(4-phenylpiperazinyl)aniline With n-butyllithium In tetrahydrofuran at -78℃; for 1.33333h; Inert atmosphere; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran at -78 - 20℃;	77.21%
Stage #1: N-benzyloxycarbonyl-3-fluoro-4-(4-phenylpiperazinyl)aniline With n-butyllithium In tetrahydrofuran at -78℃; for 1.33333h; Inert atmosphere; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran at -78 - 20℃; for 17h;	77.21%
Stage #1: N-benzyloxycarbonyl-3-fluoro-4-(4-phenylpiperazinyl)aniline With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃;

(R)-glycidyl butyrate (60456-26-0) + 2,2-dimethyl-propionic acid 4-(4-benzyloxycarbonylamino-2-fluoro-phenoxy)-piperidin-1-yl ester → 2,2-Dimethyl-propionic acid 4-[2-fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenoxy]-piperidin-1-yl ester

Conditions	Yield
Stage #1: 2,2-dimethyl-propionic acid 4-(4-benzyloxycarbonylamino-2-fluoro-phenoxy)-piperidin-1-yl ester With n-butyllithium at -78℃; Stage #2: (R)-glycidyl butyrate at -78 - 20℃;	90%

benzyl [4-(2-oxopyrrolidin-1-yl)phenyl]carbamate (348626-48-2) + (R)-glycidyl butyrate (60456-26-0) → (5R)-5-(hydroxymethyl)-3-[4-(2-oxopyrrolidin-1-yl)phenyl]-1,3-oxazolidin-2-one (348626-49-3)

Conditions	Yield
Stage #1: benzyl [4-(2-oxopyrrolidin-1-yl)phenyl]carbamate With n-butyllithium; i-Amyl alcohol In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃;	90%
With n-butyllithium In tetrahydrofuran; diethyl ether; hexane; water

C14H12BrNO3 + (R)-glycidyl butyrate (60456-26-0) → (R)-3-(4-bromo-3-hydroxyphenyl)-5-(hydroxymethyl)oxazolidin-2-one

Conditions	Yield
Stage #1: C14H12BrNO3 With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.33333h; Inert atmosphere; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;	90%

C26H37FN2O3Si (1097722-43-4) + (R)-glycidyl butyrate (60456-26-0) → C22H35FN2O4Si (1097722-44-5)

Conditions	Yield
Stage #1: C26H37FN2O3Si With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran at -78 - 25℃;	89%

(4-benzyloxy-3-fluorophenyl)carbamic acid benzyl ester (790703-40-1) + (R)-glycidyl butyrate (60456-26-0) → (R)-3-(4-benzyloxy-3-fluoro-phenyl)-5-(hydroxymethyl)-oxazolidin-2-one (790703-49-0)

Conditions	Yield
Stage #1: (4-benzyloxy-3-fluorophenyl)carbamic acid benzyl ester With lithium hexamethyldisilazane In tetrahydrofuran; hexane at 20℃; for 1h; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at 0 - 20℃; for 0.5h; Stage #3: With sodium methylate In tetrahydrofuran; methanol; hexane for 0.25h; Reagent/catalyst; Solvent;	88.5%
Stage #1: (4-benzyloxy-3-fluorophenyl)carbamic acid benzyl ester With lithium hexamethyldisilazane In tetrahydrofuran; hexane at 20℃; for 1h; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #3: With sodium methylate In tetrahydrofuran; methanol; hexane at 20℃; for 0.25h;	88.5%
Stage #1: (4-benzyloxy-3-fluorophenyl)carbamic acid benzyl ester With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane for 0.5h;	87%
With n-butyllithium at -60℃; for 24h;	80%
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.25h; Cooling with acetone-dry ice;	65.5%

C28H37FN4O6 (952150-16-2) + (R)-glycidyl butyrate (60456-26-0) → 5(R)-(hydroxymethyl)-3-(3-fluoro-4-(1-(benzyloxycarbonyl)-2-(tert-butoxycarbonyl)[1,2,5]triazepan-5-yl)phenyl)oxazolidin-2-one (952150-17-3)

Conditions	Yield
Stage #1: C28H37FN4O6 With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at 20℃; for 0.333333h; Stage #3: With potassium carbonate In methanol at 20℃; for 6h;	88%
Stage #1: C28H37FN4O6 With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃; Stage #3: With potassium carbonate In methanol at 20℃; for 6h;	88%

(3,4-Dichloro-phenyl)-carbamic acid benzyl ester (70875-62-6) + (R)-glycidyl butyrate (60456-26-0) → C10H9Cl2NO3 (677727-45-6)

Conditions	Yield
Stage #1: (3,4-Dichloro-phenyl)-carbamic acid benzyl ester With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃;	88%

(R)-glycidyl butyrate (60456-26-0) + N-carbobenzoxy-3-fluoro-4-(N-carbobenzoxypiperazin-1-yl)aniline (174649-03-7, 1026663-92-2) → (R)-[N-3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]methanol (174649-04-8)

Conditions	Yield
Stage #1: N-carbobenzoxy-3-fluoro-4-(N-carbobenzoxypiperazin-1-yl)aniline With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -60 - 20℃;	87%
Stage #1: N-carbobenzoxy-3-fluoro-4-(N-carbobenzoxypiperazin-1-yl)aniline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.63333h; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃; for 22.1h;	85%
Stage #1: N-carbobenzoxy-3-fluoro-4-(N-carbobenzoxypiperazin-1-yl)aniline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃; for 4.5h;	82%
With n-butyllithium 1.) THF, hexane, -78 deg C, 1.5 h, 2.) THF, hexane, a) -78 deg C, 1 h, b) RT, 3.5 h; Yield given. Multistep reaction;
With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere;

(1α,5α,6α)-3-(4-benzyloxycarbonylamino-2,6-difluorophenyl)-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester (681424-90-8) + (R)-glycidyl butyrate (60456-26-0) → (R)-(1α,5α,6α)-3-[2,6-difluoro-4-(5-hydroxymethyl-2-oxooxazolidin-3-yl)phenyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester (681425-00-3)

Conditions	Yield
Stage #1: (1α,5α,6α)-3-(4-benzyloxycarbonylamino-2,6-difluorophenyl)-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.5h; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran at 20℃; for 16h;	87%

5-(4-benzyloxycarbonylamino-2,6-difluorophenyl)[1,2,5]oxadiazepane-2-carboxylic acid tert-butyl ester (952151-42-7) + (R)-glycidyl butyrate (60456-26-0) → 5(R)-(hydroxymethyl)-3-(3,5-difluoro-4-(2-(tertbutoxycarbonyl)[1,2,5]oxadiazepan-5-yl)phenyl)oxazolidin-2-one (952151-43-8)

Conditions	Yield
Stage #1: 5-(4-benzyloxycarbonylamino-2,6-difluorophenyl)[1,2,5]oxadiazepane-2-carboxylic acid tert-butyl ester With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃; for 19.1667h; Stage #3: With potassium carbonate In methanol for 0.25h;	87%
Stage #1: 5-(4-benzyloxycarbonylamino-2,6-difluorophenyl)[1,2,5]oxadiazepane-2-carboxylic acid tert-butyl ester With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Inert atmosphere; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃; for 23.1667h; Inert atmosphere;	87%
Stage #1: 5-(4-benzyloxycarbonylamino-2,6-difluorophenyl)[1,2,5]oxadiazepane-2-carboxylic acid tert-butyl ester; (R)-glycidyl butyrate With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 19.3h; Inert atmosphere; Stage #2: With potassium carbonate In methanol for 0.25h;	87%

[4-(3,6-dihydro-2H-pyridin-1-yl)-3-fluoro-phenyl]-carbamic acid benzyl ester (847256-99-9) + (R)-glycidyl butyrate (60456-26-0) → 3-[4-(3,6-dihydro-2H-pyridin-1-yl)-3-fluoro-phenyl]-5-hydroxymethyl-oxazolidin-2-one (847257-16-3)

Conditions	Yield
Stage #1: [4-(3,6-dihydro-2H-pyridin-1-yl)-3-fluoro-phenyl]-carbamic acid benzyl ester With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran at -78 - 20℃;	87%

(4-bromo-3-fluorophenyl)carbamic acid benzyl ester (510729-01-8) + (R)-glycidyl butyrate (60456-26-0) → (5R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one (444335-16-4)

Conditions	Yield
With lithium tert-butoxide In tetrahydrofuran; methanol; N,N-dimethyl-formamide at 0 - 20℃; for 3h;	87%
Stage #1: (4-bromo-3-fluorophenyl)carbamic acid benzyl ester With lithium tert-butoxide In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; methanol; N,N-dimethyl-formamide at 20℃; for 3h;	87%
Stage #1: (4-bromo-3-fluorophenyl)carbamic acid benzyl ester With n-butyllithium In tetrahydrofuran; hexane; tert-butyl alcohol at 0℃; for 0.5h; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane; tert-butyl alcohol at 0 - 20℃;	86.4%

4-(((benzyloxy)carbonyl)amino)-2-fluorobenzoic acid (1087353-56-7) + (R)-glycidyl butyrate (60456-26-0) → (R)-2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)benzoic acid

Conditions	Yield
Stage #1: 4-(((benzyloxy)carbonyl)amino)-2-fluorobenzoic acid With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.33333h; Inert atmosphere; Stage #2: (R)-glycidyl butyrate In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;	87%

Upstream product

• 2461-40-7 (+/-)-glycidyl butyrate 
• 141-75-3 butyryl chloride 
• 60456-23-7 (S)-oxiranemethanol 
• 123-20-6 vinyl n-butyrate 
• 106-31-0 butanoic acid anhydride 
• 890051-54-4 butyric acid-3-chloro-(S)-2-hydroxy-propyl ester 

Downstream Products

• 168828-82-8 (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol 
• 168828-72-6 (R)-<3-<3-fluoro-4-(4-thiomorpholinyl)phenyl>-2-oxo-5-oxazolidinyl>methanol 
• 174649-04-8 (R)-[N-3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]methanol 
• 87508-42-7 (R)-5-(hydroxymethyl)-3-phenyl-2-oxooxazolidine 
• 252328-82-8 MMV₆₈₇₇₂₉ 
• 346665-75-6 (R)-3-[4-(1-Benzhydryl-azetidin-3-yloxy)-3-fluoro-phenyl]-5-hydroxymethyl-oxazolidin-2-one 
• 196299-06-6 3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-imidazol-1-yl]-3-fluoro-phenyl}-5-(R)-hydroxymethyl-oxazolidin-2-one 
• 1027839-28-6 {1-[2-fluoro-4-(5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-1H-pyrazol-3-yl}-carbamic acid tert-butyl ester 
• 1025890-48-5 (R)-3-[4-(3-Acetyl-pyrrol-1-yl)-3-fluoro-phenyl]-5-hydroxymethyl-oxazolidin-2-one 
• 181997-26-2 (R)-[3-[3-fluoro-4-(2H-1,2,3-triazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methanol 
• 1027270-98-9 (R)-[3-[3-fluoro-4-(2H-1,2,3,4-tetrazol-2-yl)phenyl]-2-oxo-5-oxazolidinyl]methanol 
• 181997-23-9 (R)-[3-[3-fluoro-4-(1H-1,2,3-triazol-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methanol 

Relevant articles and documents

Enhanced catalytic activity of lipase in situ encapsulated in electrospun polystyrene fibers by subsequent water supply

Rhizopus oryzae lipase prepared was immobilized in polystyrene electrospun fibers from a suspension of crude lipase powder in an N,N-dimethylformamide solution of polystyrene. The performance of the enzyme was enhanced by supplying water onto the resultant non-woven fabric. The electrospun fibers supplied with water by spraying showed 47-fold faster initial transesterification rate measured as conversion of (S)-glycidol to glycidyl n-butyrate with vinyl n-butyrate compared with a non-encapsulated crude lipase control. Before being moistened with water, the initial transesterification rate was slower than non-encapsulated lipase. The encapsulated and moistened lipase showed 77% of residual activity after 10 cycles of use.

Synthesis and enzymatic resolution of racemic 2,3-epoxy propyl esters obtained from glycerol

A method is described for the synthesis of (±)-2,3-epoxy propyl esters from glycerol, involving reaction of epichlorohydrin with sodium or potassium salts of carboxylic acids in the presence of TBAB as catalyst, with moderate to excellent yields. Kinetic resolution of glycidyl butyrate by lipase of Thermomyces lanuginosa has been achieved with remarkable enantiomeric excess (ee >99%) using 1,4-dioxane as a co-solvent in pure buffer solution (30 and 50 °C, pH = 7.0).

Stereoselective synthesis of (R)-glycidyl butyrate from racemic glycidyl butyrate or epichlorohydrin via hydrolytic kinetic resolution

The differences of (R)-glycidyl butyrate synthesis via hydrolytic kinetic resolution of glycidyl butyrate directly or regioselective opening epichlorohydrin as key steps by using Jacobsen's hydrotic kinetic resolution are compared. In the view of separation problem, it is hard to get the pure (R)-glycidyl butyrate by kinetic resolution of glycidyl butyrate directly. Via kinetic resolution of epichlorohydrin, treatment with butyric acid in the presence of CrCl3 and then epoxidation with NaOH, the total yield of 38.5% and optical purity of 99% are obtained.