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 language | English |
---|---|
Pages (from-to) | 2887-2893 |
Number of pages | 7 |
Journal | Carbohydrate Research |
Volume | 343 |
Issue number | 17 |
DOIs | |
Publication status | Published - 2008 Nov 24 |
All Science Journal Classification (ASJC) codes
- Analytical Chemistry
- Biochemistry
- Organic Chemistry