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在腈类溶剂中，使用1-金刚烷基硫代唾液酸苷于-78℃进行α-选择性唾液酸化反应。

alpha-selective sialylations at -78 degrees C in nitrile solvents with a 1-adamantanyl thiosialoside.

作者信息

Crich David, Li Wenju

机构信息

Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.

出版信息

J Org Chem. 2007 Sep 28;72(20):7794-7. doi: 10.1021/jo7012912. Epub 2007 Sep 7.

DOI:10.1021/jo7012912
PMID:17824651
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3102260/
Abstract

Novel 1-adamantanylthio sialosides were synthesized and coupled to acceptors under NIS/TfOH promotion conditions. These donors showed higher reactivity than the phenylthio sialosides and could be activated by NIS/TfOH in nitrile solvents at -78 degrees C to afford improved alpha-sialylations. With the N-acetyl-5-N,4-O-oxazolidinone-protected 1-adamantanylthio sialyl donor high alpha-selectivities could be achieved in the sialylations of both primary and sterically hindered secondary acceptors, including the important galactose 3-OH acceptors.

摘要

合成了新型1-金刚烷基硫代唾液酸苷，并在NIS/TfOH促进条件下与受体偶联。这些供体比苯硫基唾液酸苷具有更高的反应活性，并且在腈类溶剂中于-78℃可被NIS/TfOH活化，以实现改进的α-唾液酸化反应。使用N-乙酰基-5-N,4-O-恶唑烷酮保护的1-金刚烷基硫代唾液酸供体，在伯受体和空间位阻仲受体（包括重要的半乳糖3-OH受体）的唾液酸化反应中均可实现高α-选择性。