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Synthesis of a useful anomeric thioacetate of an N-acetyllactosamine derivative and its application

✍ Scribed by Koji Matsuoka; Takumi Ohtawa; Hiroshi Hinou; Tetsuo Koyama; Yasuaki Esumi; Shin-Ichiro Nishimura; Ken Hatano; Daiyo Terunuma

Book ID
104253486
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
183 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

A novel anomeric b-thioacetate of an N-acetyllactosamine derivative was efficiently synthesized in high yield from the known 2-azido glycosyl chloride using thioacetic acid as a convenient reagent. The synthesis involved not only an S N 2 replacement of the chloride by a carbothiolate anion but also a reductive acetamidation of the azide group. Applications of the thioacetate for glycosidation were demonstrated to provide both O-and S-glycosides in high yields. Furthermore, both intermediates gave a new class of glycoclusters that included thioglycosidic linkages.

πŸ“œ SIMILAR VOLUMES

ChemInform Abstract: Regiospecific Synth
ChemInform Abstract: Regiospecific Syntheses of N-Acetyllactosamine Derivatives and Application Toward a Highly Practical Synthesis of Lewis X Trisaccharide.
✍ Zhonghong Gan; Suoding Cao; Qingquan Wu; Rene Roy πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 33 KB πŸ‘ 2 views

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