Efficient and Stereoselective Synthesis of α(2→9) Oligosialic Acids: From Monomers to Dodecamers

Efficient and Stereoselective Synthesis of α(2→9) Oligosialic Acids: From Monomers to Dodecamers

The chain gang: The α(2→9) dodecasialic acid has been stereoselectively synthesized in 12 steps by using a convergent block synthesis (see scheme). The use of chloroacetyl protecting groups and a phosphate group as a leaving group led to the improvement of the α selectivity of the glycosylation reac...

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Veröffentlicht in:Angewandte Chemie International Edition 2011-09, Vol.50 (40), p.9391-9395
Hauptverfasser: Chu, Kuo-Ching, Ren, Chien-Tai, Lu, Chun-Ping, Hsu, Che-Hsiung, Sun, Tsung-Hsien, Han, Jeng-Liang, Pal, Bikash, Chao, Tsung-An, Lin, Yung-Feng, Wu, Shih-Hsiung, Wong, Chi-Huey, Wu, Chung-Yi
Format: Artikel
Sprache:eng
Schlagworte:
block synthesis
Carbohydrate Conformation
Carbohydrate Sequence
Chemistry Techniques, Synthetic - methods
Electrophoresis, Capillary
Glycosylation
Hydrolysis
Molecular Structure
N-Acetylneuraminic Acid - chemistry
Neuraminidase - chemistry
Neuraminidase - metabolism
oligosaccharides
Sialic Acids - chemical synthesis
Sialic Acids - chemistry
Stereoisomerism
structure elucidation
synthetic methods
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Zusammenfassung:The chain gang: The α(2→9) dodecasialic acid has been stereoselectively synthesized in 12 steps by using a convergent block synthesis (see scheme). The use of chloroacetyl protecting groups and a phosphate group as a leaving group led to the improvement of the α selectivity of the glycosylation reactions, thus allowing synthesis of oligomers.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201101794