Stereoselective synthesis of protected 3-amino-3,6-dideoxyaminosugars.
New syntheses of densely functionalized protected derivatives of 3-amino-3,6-dideoxyaminosugars have been accomplished in an efficient and straightforward manner. The key step of such approaches involves a highly stereoselective titanium-mediated aldol addition of a chiral α-bromo ketone, easily available from lactate esters, to crotonaldehyde. Further functional group transformations, including a new regioselective Staudinger-aza-Wittig reaction of an azidodiacetate, afford in a few steps and high yield the desired carbohydrates as advanced intermediates capable of participating in subsequent glycosylation reactions.
Departament de Química Orgànica, Universitat de Barcelona, Martí i Franqués 1-11, 08028 Barcelona, Catalonia, Spain.
Joaquim
J
Nebot
Pedro
P
Romea
Fèlix
F
Urpí
D000447:Aldehydes / Q000737:chemistry; D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D003847:Deoxyglucose / Q000031:analogs & derivatives / Q000138:chemical synthesis; D006595:Hexosamines / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry
D000447:Aldehydes; D000606:Amino Sugars; D006595:Hexosamines; C014692:mycosamine; C116609:3-hydroxybutanal; D003847:Deoxyglucose; D014025:Titanium