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Details for article 3 of 111 found articles
| Title: |
Alkylidenation of Sugar Lactones and Further Transformation to C-Glycosides |
| Author: |
Xie, Juan Molina, Adeline Czernecki, Stanislas |
| Appeared in: |
Journal of carbohydrate chemistry |
| Paging: | Volume 18 (1999) nr. 5 pages 481-498 |
| Year: |
1999 |
| Contents: |
The Witting reaction of (carbethoxymethylene)triphenylphosphorane with perbenzylated sugar δ-lactones and their 2-acetamido-2-deoxy derivatives is described. It is shown that this olefination occurred readily with the galacto and gluco derivatives, leading stereoselectively to Z-C-glycosylidenes in good yields. However, the same reaction with the perbenzylated 2-deoxy-D-arabino-hexono-1,5-lactone and the mannonolactones worked poorly. Reduction over Pd/C followed by acetylation of the obtained C-glycosylidenes led stereoselectively to peracetylated β-C-glycosides and amino β-C-glycosides. The olefin function could also be reduced selectively by Raney nickel or NiCl2/NaBH4, affording the perbenzylated C-glycosides and amino β-C-glycosides. Other transformation of the enol ether function is also reported. |
| Publisher: |
Taylor & Francis |
| Source file: |
Elektronische Wetenschappelijke Tijdschriften |
Details for article 3 of 111 found articles
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