Acetic Anhydride → HCID 178476369, compound

HRID 991141Notes

Reaction equation

HRID 991141 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:7][C:6](=[O:8])[C:5](=[C:9]([NH:11][C@@H:12]2[C@@H:18]([OH:19])[C@H:17]([OH:20])[C@@H:16]([CH2:21][OH:22])[O:15][CH:13]2[OH:14])[CH3:10])[C:4](=[O:23])[CH2:3]1.C(O[C:29](=[O:31])[CH3:30])(=O)C>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:24])[CH2:7][C:6](=[O:8])[C:5](=[C:9]([NH:11][C@@H:12]2[C@@H:18]([O:19][C:13](=[O:14])[CH3:12])[C@H:17]([O:20][C:16](=[O:15])[CH3:17])[C@@H:16]([CH2:21][O:22][C:29](=[O:31])[CH3:30])[O:15][C@@H:13]2[O:14][C:6](=[O:8])[CH3:5])[CH3:10])[C:4](=[O:23])[CH2:3]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178464542HCID 178464542, compound

Product 1

HCID 178476369HCID 178476369, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-amino]-D-glucopyranose (1.55 g, 4.51 mmol), pyridine (11 ml) and acetic anhydride (20 ml) was stirred at room temperature overnight. The reaction mixture was evaporated, and the product was crystallised from MeOH (10 ml) at −15° C. to give 2-Deoxy-2-[1-(-4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl-amino]-1,3,4,6-tetra-O-acetyl-α-D-glucopyranose (2) (1.95 g, 86%).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe product was crystallised from MeOH (10 ml) at −15° C.

Sources & evidence

ORD record
ord-2b71612af7e844d9ab25a3a7177c4361
Source dataset
uspto-grants-2002_10
Patent number
US06462183B1

Reaction notes

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