Trimethylsilylnitrate-trimethylsilyl azide: a novel reagent system for the synthesis of 2-deoxyglycosyl azides from glycals. Application in the synthesis of 2-deoxy-beta-N-glycopeptides.
A novel reagent system comprising Me(3)SiN(3) and 20 mol % of Me(3)SiONO(2) 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 Ph(3)P-H(2)O to amino functionality followed by coupling with amino acids leads to the synthesis of novel 2-deoxy-beta-N-glycopeptides irrespective of the geometry of initial azido sugars. Using this protocol, a new gamma-sugar amino acid derivative is also procured.
Reddy
B Gopal
BG
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur-208 016, India.
Madhusudanan
K P
KP
Vankar
Yashwant D
YD
D001386:Azides / Q000737:chemistry*; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D001386:Azides; D002241:Carbohydrates; D006020:Glycopeptides; D007202:Indicators and Reagents; D012821:Silanes