A Glycal Approach to the Synthesis of Pregnane Glycoside P57,Chinese Journal of Chemistry

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A Glycal Approach to the Synthesis of Pregnane Glycoside P57
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2018-09-05 , DOI: 10.1002/cjoc.201800331
Chao Liu ₁ , Yuyong Ma ₁ , Chengfeng Pei ₁ , Wei Li _{1,

2} , Biao Yu ₁

Affiliation

Pregnane glycoside P57 is known as an active component of Hoodia gordonii, which has long been used as a diet with appetite suppressant property. Chemical synthesis of P57 demands installation of β‐cymarosyl linkage onto the steroid aglycone. The stereoselective formation of this special 2‐deoxy‐β‐glycosidic linkage has previously been proven to be difficult and thus a limiting step in the synthesis of P57 and its congeners. Herein, we report the glycosylation reactions with glycals as donors and TPHB (triphenylphosphine hydrobromide) as promoter and a convergent synthesis of P57 via a β‐selective glycosylation with a trisaccharide glycal donor.

中文翻译：

甘醇糖苷P57合成的糖基方法

孕烷糖苷P57被称为Hoodia gordonii的活性成分，长期以来一直用作具有食欲抑制特性的饮食。P57的化学合成需要在类固醇糖苷配基上安装β-环糖基键。以前已证明这种特殊的2-脱氧-β-糖苷键的立体选择性形成是困难的，因此是合成P57及其同类物的限制步骤。在此，我们报道了以糖基为供体的糖基化反应和以TPHB（氢溴化三苯膦）为促进剂的糖基化反应，以及通过与三糖糖基供体的β-选择性糖基化聚合合成的P57。

更新日期：2018-09-05

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