Two synthetic approaches for 5-thio--glucopyranose (5-TDGP) and its pentaacetates were described, focusing on different protective groups such as -butyldimethylsilyl and benzoyl employed to protect 3-OH. These protective groups were easily introduced from the beginning and can be removed during transformation from the corresponding mesylate of α--glucofuranose to 5,6-episulfide under mild conditions. In addition, a few purification manipulations were required for each approach. More importantly, 5-TDGP can be prepared using the two approaches starting from 200 g of starting material in 66.08 % and 64.4 % overall yields, respectively.

中文翻译：

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5-硫代-d-吡喃葡萄糖及其五乙酸酯衍生物的温和实用合成


描述了 5-硫代-吡喃葡萄糖 (5-TDGP) 及其五乙酸盐的两种合成方法，重点关注不同的保护基团，例如用于保护 3-OH 的丁基二甲基甲硅烷基和苯甲酰基。这些保护基团从一开始就很容易引入，并且可以在温和条件下从相应的α-呋喃葡萄糖甲磺酸酯转化为5,6-环硫醚的过程中去除。此外，每种方法都需要一些纯化操作。更重要的是，使用两种方法可以从 200 g 起始材料开始制备 5-TDGP，总产率分别为 66.08 % 和 64.4 %。