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Practical preparation of 2-azido-2-deoxy-β-d-mannopyranosyl carbonates and their application in the synthesis of oligosaccharides
- Source :
-
Carbohydrate Research . Dec2007, Vol. 342 Issue 18, p2810-2817. 8p. - Publication Year :
- 2007
-
Abstract
- Abstract: 1-O-Allyloxycarbonyl (or ethyloxycarbonyl)-2-azido-2-deoxy-3-O-benzyl (or allyl, or benzoyl)-4,6-O-isopropylidene-β-d-mannopyranose derivatives were prepared from the corresponding 2-hydroxy-β-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. [Copyright &y& Elsevier]
- Subjects :
- *HYDROXYL group
*RADICALS (Chemistry)
*NEISSERIACEAE
*ACINETOBACTER
Subjects
Details
- Language :
- English
- ISSN :
- 00086215
- Volume :
- 342
- Issue :
- 18
- Database :
- Academic Search Index
- Journal :
- Carbohydrate Research
- Publication Type :
- Academic Journal
- Accession number :
- 27641073
- Full Text :
- https://doi.org/10.1016/j.carres.2007.09.001