Gopal Reddy, B. ; Madhusudanan, K. P. ; Vankar, Yashwant D. (2004) Trimethylsilylnitrate-trimethylsilyl azide: a novel reagent system for the synthesis of 2-deoxyglycosyl azides from glycals. Application in the synthesis of 2-deoxy-β-N-glycopeptides Journal of Organic Chemistry, 69 (7). pp. 2630-2633. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo0354948
Related URL: http://dx.doi.org/10.1021/jo0354948
Abstract
A novel reagent system comprising Me3SiN3 and 20 mol % of Me3SiONO2 permits conversion of glycals to 1-azido 2-deoxy sugars in one step in fair to good yields. Galactals offer higher stereoselectivities than do the glucals. Reduction of the azide group with Ph3P-H2O to amino functionality followed by coupling with amino acids leads to the synthesis of novel 2-deoxy-β-N-glycopeptides irrespective of the geometry of initial azido sugars. Using this protocol, a new γ-sugar amino acid derivative is also procured.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 58175 |
| Deposited On: | 31 Aug 2011 06:38 |
| Last Modified: | 31 Aug 2011 06:38 |
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