Water → methyl 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranoside

HRID 1779844Notes

Reaction equation

HRID 1779844 reaction equation
[CH3:1][O:2][C@H:3]1[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@H:5]([OH:12])[C@H:4]1[OH:13].[OH-].[K+].O.[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([O:13][C@@H:4]1[C@@H:5]([O:12][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:6]([O:11][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:7]([CH2:9][O:10][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:8][C@@H:3]1[O:2][CH3:1])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 14797Potassium HydroxideHCID 64947methyl alpha-D-glucopyranoside

Product 1

HCID 10840491methyl 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranoside

Procedure

Methyl-α-D-glucopyranoside 9 (75 g) is dissolved in benzyl chloride (400 mL). To this solution is added potassium hydroxide (250 g). The resulting suspension is heated at 100° C. (water bath temp.) with stirring (mechanical) for 4 h, then cooled to r.t. The mixture is washed with saturated NaCl in ether (500 mL) and dried with MgSO4. The ether is evaporated. The residue is distilled under vacuum (~0.1 mm Hg) at a temperature of 120° C. until no more distillate is collected or the temperature at the distilling head begins to fall. The pot residue is used for the next reaction without further purification.

Workup

  1. washThe mixture is washed with saturated NaCl in ether (500 mL)
  2. dry with materialdried with MgSO4
  3. customThe ether is evaporated
  4. distillationThe residue is distilled under vacuum (~0.1 mm Hg) at a temperature of 120° C. until no more distillate
  5. customis collected
  6. customThe pot residue is used for the next reaction without further purification

Sources & evidence

ORD record
ord-67acdac253c6439ebb9da8214d7bb7d6
Source dataset
uspto-grants-1997_05
Patent number
US05627270

Reaction notes

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