(R)-Glycidyl butyrate supplier

Name
(R)-Glycidyl butyrate
EINECS -0
CAS No. 60456-26-0
Article Data12
CAS DataBase
Density 1.069 g/cm³
Solubility insoluble in water
Melting Point
Formula C₇H₁₂O₃
Boiling Point 196.3 °C at 760 mmHg
Molecular Weight 144.17
Flash Point 85 °C
Transport Information UN 2810
Appearance Colorless to light yellow liquid
Safety 23-36/37-45-36/37/39-26
Risk Codes 22-36/37/38-42/43
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms Butanoicacid, (2R)-oxiranylmethyl ester (9CI);Butanoic acid, oxiranylmethyl ester,(R)-;(-)-Glycidyl butyrate;(2R)-(-)-Glycidyl butyrate;(R)-(-)-Glycidylbutyrate;
PSA 38.83000
LogP 1.11860

Synthetic route

: 890051-54-4
butyric acid-3-chloro-(S)-2-hydroxy-propyl ester

: 60456-26-0
(R)-glycidyl butyrate

Conditions

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.

: 141-75-3
butyryl chloride

: 60456-23-7
(S)-oxiranemethanol

: 60456-26-0
(R)-glycidyl butyrate

Conditions

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

: 2461-40-7
(+/-)-glycidyl butyrate

A: 5309-42-2
1-sn-monobutyroylglycerol

B: 60456-26-0
(R)-glycidyl butyrate

C: 126254-87-3
(S)-2,3-dihydroxypropyl butyrate

Conditions

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

...Expand

: 2461-40-7
(+/-)-glycidyl butyrate

A: 60456-26-0
(R)-glycidyl butyrate

B: 126254-87-3
(S)-2,3-dihydroxypropyl butyrate

Conditions

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

: 2461-40-7
(+/-)-glycidyl butyrate

A: 60456-26-0
(R)-glycidyl butyrate

B: 57044-25-4
(R)-oxiranemethanol

Conditions

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

: 2461-40-7
(+/-)-glycidyl butyrate

A: 890051-54-4
butyric acid-3-chloro-(S)-2-hydroxy-propyl ester

B: 890051-57-7
butyric acid-3-chloro-(R)-2-hydroxy-propyl ester

C: 60456-26-0
(R)-glycidyl butyrate

D: 65031-96-1
(S)-glycidyl butyrate

Conditions

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%

...Expand

: 2461-40-7
(+/-)-glycidyl butyrate

A: 60456-26-0
(R)-glycidyl butyrate

B: 126254-87-3
(S)-2,3-dihydroxypropyl butyrate

C: 65031-96-1
(S)-glycidyl butyrate

Conditions

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

...Expand

: 2461-40-7
(+/-)-glycidyl butyrate

A: 60456-26-0
(R)-glycidyl butyrate

B: 57044-25-4
(R)-oxiranemethanol

C: 60456-23-7
(S)-oxiranemethanol

Conditions

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;

...Expand

: 106-31-0
butanoic acid anhydride

: 60456-23-7
(S)-oxiranemethanol

: 60456-26-0
(R)-glycidyl butyrate

Conditions

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

: 123-20-6
vinyl n-butyrate

: 60456-23-7
(S)-oxiranemethanol

: 60456-26-0
(R)-glycidyl butyrate

Conditions

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

: 2461-40-7
(+/-)-glycidyl butyrate

A: 5309-42-2
1-sn-monobutyroylglycerol

B: 60456-26-0
(R)-glycidyl butyrate

C: 65031-96-1
(S)-glycidyl butyrate

Conditions

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

...Expand

: 1632-84-4
4-(methylthio)phenyl isocyanate

: 60456-26-0
(R)-glycidyl butyrate

: 121373-23-7
(R)-<3-<4-(methylthio)phenyl>-2-oxo-5-oxazolidinyl>methyl butyrate

Conditions

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

: 60456-26-0
(R)-glycidyl butyrate

: 1904-98-9
2,6-diaminopurine

: Butyric acid (R)-3-(2,6-diamino-purin-9-yl)-2-hydroxy-propyl ester

Conditions

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

: 60456-26-0
(R)-glycidyl butyrate

: 4-(2-fluoro-4-isothiocyanato-phenyl)-morpholine

: 760983-13-9
(R)-3-(3-Fluoro-4-morpholin-4-yl-phenyl)-5-hydroxymethyl-oxazolidine-2-thione

Conditions

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%

: 201230-82-2
carbon monoxide

: 60456-26-0
(R)-glycidyl butyrate

: (R)-4-(butyroxymethyl)-2-propiolactone

Conditions

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

: benzyl (5-iodopyridin-2-yl)carbamate

: 60456-26-0
(R)-glycidyl butyrate

: (R)-5-(hydroxymethyl)-3-(5-iodopyridin-2-yl)oxazolidin-2-one

Conditions

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

: 60456-26-0
(R)-glycidyl butyrate

: (R)-3-(3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)-5-(hydroxymethyl)oxazolidin-2-one

Conditions

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%

: 1395322-89-0
2-[4-[[(benzyloxy)carbonyl]amino]-2-fluorophenyl]-hexahydro-1H-spiro[cyclopenta[c]pyrrole-5,2'-[1,3]dioxolane]

: 60456-26-0
(R)-glycidyl butyrate

: 1395322-90-3
(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

Conditions

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%

: 1259556-26-7
1-(4-benzyloxycarbonylamino-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

: 60456-26-0
(R)-glycidyl butyrate

: 1-[(4-(5R)-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

Conditions

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%

: 1259556-26-7
1-(4-benzyloxycarbonylamino-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

: 60456-26-0
(R)-glycidyl butyrate

: 1259556-27-8
1-[4-((5R)-hydroxymethyl-2-oxooxazolidin-3-yl)phenyl]-3-azabicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

Conditions

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%

: 2603-10-3
N-phenyl methyl carbamate

: 60456-26-0
(R)-glycidyl butyrate

: 87508-42-7
(R)-5-(hydroxymethyl)-3-phenyl-2-oxooxazolidine

Conditions

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

: 60456-26-0
(R)-glycidyl butyrate

: C16H24FNO4Si

Conditions

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%

: 1443005-33-1
5-(4-benzyloxycarbonylamino-2-fluorophenyl)[1,2,5]triazepane-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

: 60456-26-0
(R)-glycidyl butyrate

: 952150-17-3
5(R)-(hydroxymethyl)-3-(3-fluoro-4-(1-(benzyloxycarbonyl)-2-(tert-butoxycarbonyl)[1,2,5]triazepan-5-yl)phenyl)oxazolidin-2-one

Conditions

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%

: 60456-26-0
(R)-glycidyl butyrate

: 344460-43-1
[4-(5,7-dihydro-pyrrolo[3,4-b]pyridin-6-yl)-3-fluoro-phenyl]-carbamic acid benzyl ester

: 344459-52-5
(5R)-3-[4-(5,7-Dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-3-fluorophenyl]-5-(hydroxymethyl)-2-oxazolidinone

Conditions

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℃;

: 60456-26-0
(R)-glycidyl butyrate

: 164149-25-1
(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-carbamic acid benzyl ester

: 741721-20-0
(R)-5-hydroxymethyl-3-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-oxazolidin-2-one

Conditions

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%

: 60456-26-0
(R)-glycidyl butyrate

: 556801-41-3
N-benzyloxycarbonyl-3-fluoro-4-(4-phenylpiperazinyl)aniline

: 465520-07-4
(R)-[N-3-(3'-fluoro-4'-(4"-phenylpiperazinyl)phenyl)-2-oxo-5-oxazolidinyl]methanol

Conditions

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℃;

: 60456-26-0
(R)-glycidyl butyrate

: 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

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%

: 348626-48-2
benzyl [4-(2-oxopyrrolidin-1-yl)phenyl]carbamate

: 60456-26-0
(R)-glycidyl butyrate

: 348626-49-3
(5R)-5-(hydroxymethyl)-3-[4-(2-oxopyrrolidin-1-yl)phenyl]-1,3-oxazolidin-2-one

Conditions

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

: 60456-26-0
(R)-glycidyl butyrate

: (R)-3-(4-bromo-3-hydroxyphenyl)-5-(hydroxymethyl)oxazolidin-2-one

Conditions

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%

: 1097722-43-4
C26H37FN2O3Si

: 60456-26-0
(R)-glycidyl butyrate

: 1097722-44-5
C22H35FN2O4Si

Conditions

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

: 790703-40-1
(4-benzyloxy-3-fluorophenyl)carbamic acid benzyl ester

: 60456-26-0
(R)-glycidyl butyrate

: 790703-49-0
(R)-3-(4-benzyloxy-3-fluoro-phenyl)-5-(hydroxymethyl)-oxazolidin-2-one

Conditions

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%

: 952150-16-2
C28H37FN4O6

: 60456-26-0
(R)-glycidyl butyrate

: 952150-17-3
5(R)-(hydroxymethyl)-3-(3-fluoro-4-(1-(benzyloxycarbonyl)-2-(tert-butoxycarbonyl)[1,2,5]triazepan-5-yl)phenyl)oxazolidin-2-one

Conditions

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%

: 70875-62-6
(3,4-Dichloro-phenyl)-carbamic acid benzyl ester

: 60456-26-0
(R)-glycidyl butyrate

: 677727-45-6
C10H9Cl2NO3

Conditions

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%

: 60456-26-0
(R)-glycidyl butyrate

: 174649-03-7, 1026663-92-2
N-carbobenzoxy-3-fluoro-4-(N-carbobenzoxypiperazin-1-yl)aniline

: 174649-04-8
(R)-[N-3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]methanol

Conditions

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;

: 681424-90-8
(1α,5α,6α)-3-(4-benzyloxycarbonylamino-2,6-difluorophenyl)-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester

: 60456-26-0
(R)-glycidyl butyrate

: 681425-00-3
(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

Conditions

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%

: 952151-42-7
5-(4-benzyloxycarbonylamino-2,6-difluorophenyl)[1,2,5]oxadiazepane-2-carboxylic acid tert-butyl ester

: 60456-26-0
(R)-glycidyl butyrate

: 952151-43-8
5(R)-(hydroxymethyl)-3-(3,5-difluoro-4-(2-(tertbutoxycarbonyl)[1,2,5]oxadiazepan-5-yl)phenyl)oxazolidin-2-one

Conditions

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%

: 847256-99-9
[4-(3,6-dihydro-2H-pyridin-1-yl)-3-fluoro-phenyl]-carbamic acid benzyl ester

: 60456-26-0
(R)-glycidyl butyrate

: 847257-16-3
3-[4-(3,6-dihydro-2H-pyridin-1-yl)-3-fluoro-phenyl]-5-hydroxymethyl-oxazolidin-2-one

Conditions

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%

: 510729-01-8
(4-bromo-3-fluorophenyl)carbamic acid benzyl ester

: 60456-26-0
(R)-glycidyl butyrate

: 444335-16-4
(5R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one

Conditions

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%

: 1087353-56-7
4-(((benzyloxy)carbonyl)amino)-2-fluorobenzoic acid

: 60456-26-0
(R)-glycidyl butyrate

: (R)-2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)benzoic acid

Conditions

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%

(R)-Glycidyl butyrate Chemical Properties

IUPAC Name:[(2R)-oxiran-2-yl]methyl butanoate
Molecular Formula:C₇H₁₂O₃
Molecular Weight:144.168380 g/mol
Appearance:Yellow liquid
Boiling Point:197 °C(lit.)
Flash Point:185 °F
alpha:-30 °(c=neat)
density:1.032 g/mL at 20 °C(lit.)
refractive index:n20/D 1.428(lit.)
storage temp.: 2-8°C
Water Solubility:insoluble
BRN:5246881
CAS DataBase Reference:60456-26-0(CAS DataBase Reference)
Synonyms of (R)-4-Glycidyl butyrate(60456-26-0):
(2R)-(-)-GLYCIDYL BUTYRATE;BUTYRIC ACID (R)-GLYCIDYL ESTER;(R)-(-)-GLYCIDYL BUTYRATE;(R)-GLYCIDYL BUTYRATE;(R)-OXIRANE-2-METHANOL BUTYRATE;R(-)-OXIRANE-2-METHANOL BUTYRATE;(R)-4-GLYCIDYL BUTYRATE;(R)-2,3-EPOXYPROPYL N-BUTYRATE
Categories of (R)-4-Glycidyl butyrate(60456-26-0):
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;Ring Systems

(R)-Glycidyl butyrate Uses

(R)-4-Glycidyl butyrate(60456-26-0) is used as a intermediate for synthesis of linezolid.

(R)-Glycidyl butyrate Safety Profile

Safety Information of (R)-4-Glycidyl butyrate(60456-26-0):
Hazard Codes:Xn,Xi
Risk Statements:22-36/37/38-42/43
22:Harmful if swallowed
36/37/38:Irritating to eyes, respiratory system and skin
42/43:May cause sensitization by inhalation and skin contact
Safety Statements:23-36/37-45-36/37/39-26
23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)
36/37:Wear suitable protective clothing and gloves
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
RIDADR:2810
WGK Germany:3
F:10-21
HazardClass:6.1
PackingGroup:III

Product Name

(R)-Glycidyl butyrate

Synthetic route

(R)-Glycidyl butyrate Chemical Properties

(R)-Glycidyl butyrate Uses

(R)-Glycidyl butyrate Safety Profile

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