ChemicalBook CAS DataBase List 2,3,4,6-TETRA-O-BENZYL-D-GALACTOPYRANOSE

2,3,4,6-TETRA-O-BENZYL-D-GALACTOPYRANOSE synthesis

11synthesis methods

Product Name:2,3,4,6-TETRA-O-BENZYL-D-GALACTOPYRANOSE
CAS Number:6386-24-9
Molecular formula:C34H36O6
Molecular Weight:540.65

Methyl 2,3,4,6-Tetra-O-benzyl-a-D-galactopyranoside

53008-63-2
84 suppliers
$50.00/5G

2,3,4,6-TETRA-O-BENZYL-D-GALACTOPYRANOSE

6386-24-9
59 suppliers
$96.31/1G

Yield:6386-24-9 87%

Reaction Conditions:

with hydrogenchloride;strontium (III) chloride hexahydrate in water;acetic acid at 70;

Steps:

B. Synthesis of 2,3,4,6-Tetra-O-benzyl-D-glycopyranoses 3, 5 and 11.

General procedure: To a stirred solution of methyl 2,3,4,6-tetra-O-benzyl-α-D-glycopyranosides 3-2, 4 5-2 or 11-2 (4.99 g, 9 mmol) in 25 mL of glacial acetic acid containing SrCl₂·6H₂O (0.24 g, 0.9 mmol) heated at 70°C was added 4 mL of 5 M hydrochloric acid. The stirring was continued at 70°C until reaction completed as indicated by TLC analysis (typically within 2-3 h). The reaction mixture was poured into 300 mL of ice-water while stirring immediately after the reaction completed, and the resulting mixture was extracted with three 100-mL portions of dichloromethane. The combined extracts were washed successively with saturated sodium bicarbonate and brine, dried over anhydrous sodium sulfate and evaporated on a rotary evaporator to afford an oily residue, which was purified by column chromatography to yield the pure 2,3,4,6-tetra-O-benzyl-D-glycopyranoses 3, 5 and 11 as anomeric mixtures.

References:

Wei, Peng;Zhang, Datong;Gao, Zhigang;Cai, Wenqing;Xu, Weiren;Tang, Lida;Zhao, Guilong [Synthetic Communications,2015,vol. 45,# 12,p. 1457 - 1470] Location in patent:supporting information