Acetic Anhydride → HCID 18665153, compound

HRID 2393711Notes

Reaction equation

HRID 2393711 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:21]([OH:22])[C@@H:20]([CH2:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:19][C@@H:11]([O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C@@H:10]1[N:32]1[C:36](=[O:37])[C:35]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:34]2[C:33]1=[O:42])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:43](OC(=O)C)(=[O:45])[CH3:44]>N1C=CC=CC=1>[C:43]([O:22][C@@H:21]1[C@@H:20]([CH2:23][O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[O:19][C@@H:11]([O:12][CH2:13][CH2:14][Si:15]([CH3:17])([CH3:16])[CH3:18])[C@H:10]([N:32]2[C:36](=[O:37])[C:35]3=[CH:38][CH:39]=[CH:40][CH:41]=[C:34]3[C:33]2=[O:42])[C@H:9]1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:45])[CH3:44]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 11169277HCID 11169277, compound2×

Product 1

HCID 18665153HCID 18665153, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-(trimethyl silyl)ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (compound 14, 8.0 g, 13.6 m mol) in pyridine (40 ml), was added acetic anhydride (10 ml) at 0° C., and the mixture was stirred for 5 hrs at room temperature, and concentrated. Column chromatography (1:2 ethyl acetate-hoxane) of the residue on silica gel (200 g) gave compound 15 (8.6 g, quantitative yield) as crystals:

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-574134757a80473eae218cec81f7111e
Source dataset
uspto-grants-1998_09
Patent number
US05808019

Reaction notes

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