Methyl and Benzyl (Ethyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-d-glucopyranosyl)uronate

Molbank Pub Date : 2024-07-09 DOI:10.3390/m1847

Hannah S. Wootton, Gavin J. Miller

引用次数: 0

Abstract

Methyl and benzyl (ethyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-D-glucopyranosyl)uronate were synthesised from a protected thioglycoside in three steps. A regioselective ring opening of the benzylidene acetal with BH3.THF generated C6-OH material, which was subsequently oxidised using biphasic TEMPO/BAIB conditions. The resultant uronic acid was esterified with either a methyl or benzyl moiety. The products were obtained on a multigram scale and fully characterised by 1H, 13C and 2D NMR, alongside MS and IR analysis.

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3,4-二-O-苄基-2-O-苯甲酰基-1-硫代-β-d-吡喃葡萄糖基）脲酸甲酯和苄酯

通过三个步骤从一种受保护的硫代糖苷合成了尿苷酸甲酯和尿苷酸苄酯（3,4-二-O-苄基-2-O-苯甲酰基-1-硫代-β-D-吡喃葡萄糖基）。用 BH3.THF 对亚苄基缩醛进行区域选择性开环，生成 C6-OH 材料，随后用双相 TEMPO/BAIB 条件对其进行氧化。生成的尿酸与甲基或苄基发生酯化反应。得到的产品为多克级，并通过 1H、13C 和 2D NMR 以及 MS 和 IR 分析进行了全面鉴定。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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Molbank

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