Practical preparation of 2-azido-2-deoxy-beta-D-mannopyranosyl carbonates and their application in the synthesis of oligosaccharides.
1-O-Allyloxycarbonyl (or ethyloxycarbonyl)-2-azido-2-deoxy-3-O-benzyl (or allyl, or benzoyl)-4,6-O-isopropylidene-beta-d-mannopyranose derivatives were prepared from the corresponding 2-hydroxy-beta-d-glucopyranosyl carbonates in high yields via triflation of the 2-hydroxyl group and subsequent SN2 displacement with azide ion. An N-acetyl-mannosamine-containing trisaccharide, a fragment of the putative O10 antigen from Acinetobacter baumannii, was efficiently synthesized using these derivatives.
Zhang
Jianjun
J
Key Lab of Pesticide Chemistry and Application Technology, Department of Applied Chemistry, China Agricultural University, Beijing 100094, China.
Yan
Shiqiang
S
Liang
Xiaomei
X
Wu
Jingping
J
Wang
Daoquan
D
Kong
Fanzuo
F
D040981:Acinetobacter baumannii / Q000737:chemistry; D002240:Carbohydrate Sequence; D002254:Carbonates / Q000138:chemical synthesis* / Q000737:chemistry*; D006595:Hexosamines / Q000737:chemistry; D008358:Mannose / Q000031:analogs & derivatives* / Q000737:chemistry*; D008969:Molecular Sequence Data; D019081:O Antigens / Q000737:chemistry; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry*
D002254:Carbonates; D006595:Hexosamines; D019081:O Antigens; D014312:Trisaccharides; C008322:mannosamine; D008358:Mannose