Synthesis of 2-iodo-2-deoxy septanosides from a d-xylose-based oxepine

Intramolecular cyclization in the absence of a glycosyl acceptor

W. Sean Fyvie, Martha D Morton, Mark W. Peczuh

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Oxidative glycosylations of the d-xylose-based oxepine 1,6-anhydro-3,4,5- tri-O-benzyl-2-deoxy-d-xylosept-1-enitol (1) using N-iodosuccinimide (NIS) are reported. The reaction produced 2-deoxy-2-iodo-α-d-idoseptanosides and 2-deoxy-2-iodo-β-d-guloseptanosides 2-9 in good yields. When limited equivalents of a glycosyl acceptor were used, or in the absence of a glycosyl acceptor, an intramolecular cyclization predominated to form 1,6-anhydro-3,4-di-O-benzyl-2-deoxy-2-iodo-Iα-d-idopyranose (10).

Original languageEnglish (US)
Pages (from-to)2363-2370
Number of pages8
JournalCarbohydrate Research
Volume339
Issue number14
DOIs
StatePublished - Oct 4 2004

Fingerprint

Oxepins
Glycosylation
Xylose
Cyclization
N-iodosuccinimide
idose

Keywords

  • Glycosylation
  • Oxepine
  • Septanose carbohydrates

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this

Synthesis of 2-iodo-2-deoxy septanosides from a d-xylose-based oxepine : Intramolecular cyclization in the absence of a glycosyl acceptor. / Fyvie, W. Sean; Morton, Martha D; Peczuh, Mark W.

In: Carbohydrate Research, Vol. 339, No. 14, 04.10.2004, p. 2363-2370.

Research output: Contribution to journalArticle

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