Efficient Conversion of a 1,6-Anhydro Chitobiose Derivative into the Corresponding Tetradecyl β-Glycoside Derivative by Means of Participation of a Neighboring Tetradecanamide Group
作者:
Atsushi Umino,
Hiroshi Hinou,
Hiroyoshi Kuzuhara,
Koji Matsuoka,
Daiyo Terunuma,
Shunya Takahashi,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1998)
卷期:
Volume 17,
issue 2
页码: 231-239
ISSN:0732-8303
年代: 1998
DOI:10.1080/07328309808002324
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
In the course of our studies on the synthesis of amphiphilic chitoheptaose derivatives carrying binary long hydrocarbon chains at the reducing sugar, tetradecyl 4-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-2-tetradecanamido-β-D-glucopyranoside was prepared as a model. For general applicability, the 1,6-anhydro-2-deoxy-2-tetradecanamido-β-D-glucopyranosyl moiety was employed as a precursor of the reducing end. Acetolysis of the 1,6-anhydro ring using triethylsilyl triflate gave an oxazoline intermediate as a major product, accompanied by α-glycosyl acetate as a by-product. Immediate treatment of the mixture with 1-tetradecanol and protic acid followed by a separation work-up efficiently led to tetradecyl β-glycoside derivative.
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