| Identification | Back Directory | [Name]
1,4:3,6-Dianhydro-D-glucitol 2-acetate | [CAS]
13042-39-2 | [Synonyms]
2-Acetyl-isosorbide
Isosorbide Impurity 5
Isosorbide Impurity 15
Isosorbide Dinitrate Impurity 5
1,4:3,6-dianhydro-D-glucitol 2-acetate
1,4:3,6-Dianhydro-2-O-acetyl-D-glucitol
D-Glucitol, 1,4:3,6-dianhydro-, 2-acetate
(3S,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl acetate
(6-Hydroxy-2,3,3a,5,6,6a-hexahydrofuro[2,3-d]furan-3-yl) acetate
(6-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl) acetate
(6-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl) ethanoate
Acetic acid (3S,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl ester
acetic acid (6-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl) ester | [EINECS(EC#)]
235-917-7 | [Molecular Formula]
C8H12O5 | [MDL Number]
MFCD09264290 | [MOL File]
13042-39-2.mol | [Molecular Weight]
188.18 |
| Hazard Information | Back Directory | [Chemical Properties]
Isosorbide-2-acetate is a colourless, crystalline substance with a melting point of 75°-76°C. It has a TLC (diethyl ether) value of Rf=0.28 and a specific rotation of [α]D 20 =+77.1° (c=1.12, ethyl acetate). It is an important intermediate in the synthesis of isosorbide-5-mononitrate, a well-known organic nitrate drug. | [Uses]
1,4:3,6-Dianhydro-2-O-acetyl-D-glucitol is a useful reagent in the practical enzymic synthesis of isosorbide-2-acetate. | [Preparation]
The synthesis of isosorbide-2-acetate involves dissolving 2.30 g (10 mmol) of isosorbide-2,5-diacetate in 15 ml of acetone and 5 ml of n-heptanol. Then, 200 mg of lipase from Pseudomonas fluorescens (SAM II, Amano Pharmaceuticals) is added, and the mixture is stirred at room temperature for 2 days. After that, the enzyme is removed by filtration, and the resulting solid is washed thoroughly with acetone. The solvent, excess n-heptanol, and heptyl acetate residue are removed by distillation.
The yield is 1.71 g (9.09 mmol) of isosorbide-2-acetate, which is a colourless crystalline substance with a melting point of 75°-76°C. The overall yield is 91%.
US5538891A |
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