Solid-Phase Synthesis of Glycosyl Phosphate Repeating Units via Glycosyl Boranophosphates as Stable Intermediates,Organic Letters

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Solid-Phase Synthesis of Glycosyl Phosphate Repeating Units via Glycosyl Boranophosphates as Stable Intermediates
Organic Letters ( IF 4.9 ) Pub Date : 2023-05-19 , DOI: 10.1021/acs.orglett.3c01293
Kazuki Sato ₁ , Kazumasa Muramoto ₁ , Tomoya Hagio ₁ , Rintaro I Hara _{1,

2} , Takeshi Wada ₁

Affiliation

Solid-phase synthesis of glycosyl phosphate repeating units was investigated using glycosyl boranophosphates as stable precursors. The stable nature of glycosyl boranophosphate enables the elongation of a saccharide chain without remarkable decomposition. After deprotection of the boranophosphotriester linkages to boranophosphodiesters, the intersugar linkages were converted to the phosphate counterparts quantitatively using an oxaziridine derivative. This method significantly improves the synthesis of oligosaccharides containing glycosyl phosphate units.

中文翻译：

通过糖基硼磷酸盐作为稳定中间体固相合成糖基磷酸重复单元

使用糖基硼磷酸盐作为稳定前体研究了糖基磷酸重复单元的固相合成。糖基硼磷酸酯的稳定性质使得糖链能够延长而不会显着分解。将硼烷磷酸三酯键脱保护为硼烷磷酸二酯后，使用氧氮丙啶衍生物将糖间键定量转化为磷酸盐对应物。该方法显着改善了含有糖基磷酸单元的寡糖的合成。

更新日期：2023-05-19

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