Syringaldehyde → 4-Formyl-2,6-dimethoxyphenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside

HRID 1588195Notes

Reaction equation

HRID 1588195 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@@H:6]1Cl)(=[O:3])[CH3:2].[CH:25](=[O:37])[C:26]1[CH:36]=[C:33]([O:34][CH3:35])[C:31]([OH:32])=[C:28]([O:29][CH3:30])[CH:27]=1>CC(C)=O.[OH-].[K+].O>[C:1]([NH:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[O:32][C:31]1[C:33]([O:34][CH3:35])=[CH:36][C:26]([CH:25]=[O:37])=[CH:27][C:28]=1[O:29][CH3:30])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 8655SyringaldehydeHCID 111006222-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glucopyranosyl chloride

Product 1

HCID 544575424-Formyl-2,6-dimethoxyphenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

A solution of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride (18.3 g, 50 mmol) in acetone (100 ml) was added to a solution of syringaldehyde (9.1 g, 50 mmol) in 1M potassium hydroxide solution (100 ml). The mixture was then stirred for 18 h and then diluted with water. The precipitated crystalline solid (10.8 g, 42%) was then filtered off, washed well with water and recrystallised from acetone-water water to give the title compound, m.p. 222°-225°, [α]D +3° (c 0.9, CHCl3)

Workup

  1. filtrationThe precipitated crystalline solid (10.8 g, 42%) was then filtered off
  2. washwashed well with water
  3. customrecrystallised from acetone-water water

Sources & evidence

ORD record
ord-6294c7697e964669aba8b7c172dfac37
Source dataset
uspto-grants-1993_06
Patent number
US05221606

Reaction notes

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