以l -阿拉伯糖为原料，通过新型还原环收缩反应和pummer型硫代糖基化合成4′-硫代核糖核苷

Q4 Chemistry

Current Protocols in Nucleic Acid Chemistry Pub Date : 2018-02-13 DOI:10.1002/cpnc.45

Hideaki Wakamatsu, Kozue Nitta, Nozomi Shoji, Yoshihiro Natori, Yukako Saito, Yuichi Yoshimura

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Practical Synthesis of 4′-Thioribonucleosides from L-Arabinose via Novel Reductive Ring-Contraction Reaction and Pummerer-Type Thioglycosylation

The detailed practical synthesis of 4′-thionucleosides starting from L-arabinose is described here. 1,4-Anhydro-2,3-O-isopropylidene-4-thioribitol, which is the key intermediate for the synthesis of 4′-thionucleosides, is obtained from L-arabinose in several steps, including a novel reductive ring-contraction reaction. After oxidation of the key intermediate, the sulfoxide is subjected to Pummerer-type thioglycosylation in the presence of persilylated nucleobases to obtain the 4′-thioribonucleosides in good yield and β-selectively. © 2017 by John Wiley & Sons, Inc.

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Current Protocols in Nucleic Acid Chemistry Chemistry-Organic Chemistry

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期刊介绍： Published in association with International Society for Nucleosides, Nucleotides & Nucleic Acids (IS3NA) , Current Protocols in Nucleic Acid Chemistry is equally valuable for biotech, pharmaceutical, and academic labs. It is the resource for designing and running successful research projects in the rapidly growing and changing field of nucleic acid, nucleotide, and nucleoside research.