Methanol → 1,6-Anhydro-4-O-benzyl-3-deoxy-beta-D-erythro-hexopyranos-2-ulose dimethyl acetal

HRID 728211Notes

Reaction equation

HRID 728211 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@H:14]2[CH2:15][O:16][C@H:12]([O:13]2)[C:11](=[O:17])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18](Cl)(Cl)Cl.[CH3:22][OH:23]>Cl>[CH3:22][O:23][C:11]1([O:17][CH3:18])[CH2:10][C@H:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C@H:14]2[CH2:15][O:16][C@@H:12]1[O:13]2

Participants

5

Reactant 3

HCID 887MethanolHCID 6212ChloroformHCID 679307441,6-Anhydro-4-O-benzyl-3-deoxy-beta-D-erythro-hexopyranos-2-ulose

Product 1

HCID 679308651,6-Anhydro-4-O-benzyl-3-deoxy-beta-D-erythro-hexopyranos-2-ulose dimethyl acetal

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1,6-Anhydro-4-O-benzyl-3-deoxy-β-D-erythro-hexopyranos-2-ulose (Example 6) (0.30 g) was dissolved in 3% HCl in dry methanol (10 ml) and the solution allowed to stand at room temperature for 0.5 h. Chloroform was added and the solution was washed with saturated aqueous sodium hydrogen carbonate, water, dried (MgSO4), and concentrated to a syrup. Purification by flash chromatography on silica gel gave the title compound (0.29 g) [α]D -52.1°; 13C-nmr data: 99.6 (C-1), 96.8 (C-2), 29.0 (C-3), 72.6 (C-4), 74.6 (C-5), 65.9 (C-6), 70.6 (PhCH2O), 138.1, 128.5, 127.7 and 127.6 (aromatic), 49.1 and 47.9 (OCH3).

Workup

  1. washthe solution was washed with saturated aqueous sodium hydrogen carbonate, water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated to a syrup
  4. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e56b2c355de6462cb1be9e4371c32aab
Source dataset
uspto-grants-1991_09
Patent number
US05047518

Reaction notes

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