Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1388425 | Carbohydrate Research | 2008 | 7 Pages |
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.
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Related Topics
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Organic Chemistry
Authors
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,