HCID 22841876, compound → HCID 53932422, compound

HRID 1461460Notes

Reaction equation

HRID 1461460 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C@@H:17]1[O:38][C@H:37]([C:39]([O:41][CH3:42])=[O:40])[C@@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:23]([O:24]CC2C=CC=CC=2)[C@H:18]1[O:19][C:20](=[O:22])[CH3:21])=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C@@H:17]1[O:38][C@H:37]([C:39]([O:41][CH3:42])=[O:40])[C@@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:23]([OH:24])[C@H:18]1[O:19][C:20](=[O:22])[CH3:21])=[O:4]

Participants

4

Reactant 1

HCID 22841876HCID 22841876, compound

Product 1

HCID 53932422HCID 53932422, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 11 (30 mg) in 2 mL of methanol was hydrogenated in the presence of 5% Pd/C (10 mg) for 24 hours. The reaction was monitored by TLC. The suspension was filtered and, after complete evaporation of the solvent and chromatography, pure methyl 1-O-(11-methoxycarbonylundecyl)-2, 4-di-O-acetyl-β-D-glucopyranosuronate (12) was obtained. The 1H NMR data confirmed the complete debenzylation.

Workup

  1. filtrationThe suspension was filtered
  2. customafter complete evaporation of the solvent and chromatography

Sources & evidence

ORD record
ord-5172c33f9eef4d288804d265bac06286
Source dataset
uspto-grants-1991_12
Patent number
US05075433

Reaction notes

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