对全-O-TMS 保护的单糖进行选择性乙酰化。
Selective acetylation of per-O-TMS-protected monosaccharides.
机构信息
Department of Chemistry, University of California, Davis, 1 Shields Avenue, Davis, California 95616, USA.
出版信息
Org Lett. 2010 Oct 1;12(19):4312-5. doi: 10.1021/ol101751d.
Abstract
Selective acetylation of various per-O-TMS-protected carbohydrates has been accomplished. Using a protecting group exchange strategy and microwave assistance, monosaccharides (glucose, galactose, and mannose) can be selectively acetylated producing either the 6-O-monoacetate or 1,6-O-diacetylated species. This new class of molecules can be deprotected without migration of the acetyl groups, providing useful synthetic intermediates. To demonstrate the scope of the reaction, the methodology was successfully extended to TMS-protected ceramide.
摘要
已经实现了对各种全-O-TMS 保护的碳水化合物的选择性乙酰化。使用保护基交换策略和微波辅助，可以选择性地对单糖（葡萄糖、半乳糖和甘露糖）进行乙酰化，生成 6-O-单乙酰化物或 1,6-O-二乙酰化物。这些新的分子可以在不迁移乙酰基的情况下脱保护，提供有用的合成中间体。为了证明反应的范围，该方法成功地扩展到了 TMS 保护的神经酰胺。
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