Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5223412 | Tetrahedron | 2010 | 14 Pages |
Abstract
Stereoselectivity in N-iodosuccimide (NIS)-mediated electrophilic glycosidation was examined by employing 2,4-bis-O-(trimethylsilyl)thymine and three different silyl-protected erythro-furanoid glycals 12, 16, and 18. As a result, it was found that 3,5-O-(di-t-butylsilylene)-protected 18 gave only the β-anomer (21). The remarkable stereoselectivity observed by employing 18 is discussed on the basis of its X-ray crystallographic analysis. 1-Substituted glycals gave the corresponding β-anomer, again exclusively, to provide access to 1â²-branched 2â²-deoxynucleosides.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Kazuhiro Haraguchi, Kiju Konno, Kaori Yamada, Yasuyuki Kitagawa, Kazuo T. Nakamura, Hiromichi Tanaka,