First total synthesis of a naturally occurring nucleoside disulfide: 9-(5′-Deoxy-5′-thio-β-d-xylofuranosyl)adenine disulfide

A naturally occurring nucleoside disulfide, 9-(5′-deoxy-5′-thio-β-d-xylofuranosyl)adenine disulfide, was first synthesized from d-xylose over 7 steps in 20% overall yield. The key step involved Vorbrüggen glycosylation of silylated N6-benzoyladenine with xylose diacetate moiety.

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Bibliographic Details
Published in:Chinese chemical letters 2012-09, Vol.23 (9), p.996-998
Main Authors: Ding, Hai Xin, Da, Ling Cui, Yang, Ru Chun, Cao, Ban Peng, Sun, Qi, Xiao, Qiang
Format: Article
Language:English
Subjects:
Marine sponge
Naturally occurring nucleoside
Nucleoside disulfide
Total synthesis
Vorbrüggen glycosylation
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Description
Summary:A naturally occurring nucleoside disulfide, 9-(5′-deoxy-5′-thio-β-d-xylofuranosyl)adenine disulfide, was first synthesized from d-xylose over 7 steps in 20% overall yield. The key step involved Vorbrüggen glycosylation of silylated N6-benzoyladenine with xylose diacetate moiety.
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2012.06.011