Synthesis of iminoalditol and N-alkyl iminoalditol derivatives of ribopyranosides

An Tai Wu, Pey Jiuann Wu, Wei Zou, Jiun Ly Chir, Yuan Chun Chang, Shuan Yi Tsai, Chao Qi Guo, Wei Shuan Chang, Yu Chi Hsieh

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6 Citations (Scopus)

Abstract

Iminoalditol analogs of ribopyranosides were prepared by reduction of a vinylogous urethane intermediate formed from methyl 2-C-(5-O-methanesulfonyl-β-d-ribofuranosyl)acetate (1) by treatment with sodium azide in DMF at reflux. The N-alkylated analogs were synthesized either by N-alkylation of the corresponding parent iminoaldithol or, more efficiently, from the product of the reaction of 1 with various alkylamines. The latter process involves an SN2 substitution at C-5 by the amine followed by an intramolecular hetero-Michael reaction under basic conditions. The 'aglycon' of the iminoalditol was also modified through amidation and esterification.

Original languageEnglish
Pages (from-to)2887-2893
Number of pages7
JournalCarbohydrate Research
Volume343
Issue number17
DOIs
Publication statusPublished - 2008 Nov 24

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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