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An improved synthesis of benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-d-erythro-pentofuranoside, an intermediate in the synthesis of 4′-thionucleosides

✍ Scribed by Michael R. Dyson; Paul L. Coe; Richard T. Walker

Publisher: Elsevier Science
Year: 1992
Tongue: English
Weight: 846 KB
Volume: 216
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(92)84165-o

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✦ Synopsis

Treatment of methyl 3,5-di-O-benzyl-2-deoxy-a,8-r>-erythro-pentofuranoside with a-toluenethiol and cont. hydrochloric acid gave 3,5-di-0-benzyl-2-deoxy-D-erythro-pentose dibenzyl dithioacetal (21). Mesylation of 21 and ring closure gave benzyl 3,S-di-O-benzyl-2-deoxy-l,4-dithio-a,P-L-threo-pentofuranoside. Inversion of configuration at C-4 of 21 was achieved by the Mitsunobu reaction, to produce 4-0-benzoyl-3,5-di-O-benzyl-2-deoxy-L-thr~~-pentose dibenzyl dithioacetal. Successive debenzoylation, mesylation, and ring closure then gave the title compound. Several new dithioacetal derivatives of 2-deoxyp-er_rthro-pentose were prepared in exploratory routes to the described thio sugar or as intermediates.

* Dedicated to Professor Grant Buchanan on the occasion of his 65th birthday.

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