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Synthesis of (4-benzyloxybenzyl)-2,3-di-O-benzyl-β-D-glucopyranoside
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By: Xie, Yupeng; Zhao, Yimin In order to synthesize the naturally occurring phenolic acid substituted glucopyranosides, tetra-O-α-acetyl-D-glucopyranosyl bromide was used as the starting material to react with 4-benzyloxy benzyl alc. afforded a glucopyranoside. After deacetylation. a benzylidene group was selectively added at the 4,6-positions of the glucose and the 2,3-hydroxy groups were protected with benzyl groups. By deleting the benzylidene group it gave (4-benzyloxybenzyl)-2,3-di-O-benzyl-β-D-glucopyranoside, which has free hydroxyl groups at the 4,6-positions. This compound, as an effective intermediate, could be used for the synthesis of a series of glucopyranosides substituted by natural phenolic acid at 4,6-positions. Keywords: phenolic acid benzyloxybenzyl benzyl glucopyranoside preparation |
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(2025-6-4)
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