3-O-Benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose → 3-O-Benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose

HRID 1663549Notes

Reaction equation

HRID 1663549 reaction equation
CC1(C)[O:6][CH:5]([CH:7]2[O:11][CH:10]3[O:12][C:13]([CH3:16])([CH3:15])[O:14][CH:9]3[CH:8]2[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:4][O:3]1>C(O)(=O)C>[CH3:15][C:13]1([CH3:16])[O:12][C@@H:10]2[C@@H:9]([C@@H:8]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C@@H:7]([C@H:5]([OH:6])[CH2:4][OH:3])[O:11]2)[O:14]1

Participants

3

Reactant 1

HCID 979073-O-Benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose

Product 1

HCID 110881883-O-Benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Partial hydrolysis of 30B (50 g) was achieved in 75% acetic acid in a period of 20 h. Concentration to a smaller volume and extraction with ethyl acetate yielded 30C, 40 g, (90%). Homogeneous by TLC.

Workup

  1. concentrationConcentration
  2. extractionto a smaller volume and extraction with ethyl acetate

Sources & evidence

ORD record
ord-20b6778190b04ca4b7325a97f6430657
Source dataset
uspto-grants-2011_10
Patent number
US08034909B2

Reaction notes

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