Synthesis of β-acylamino furans from glucosamine

A facile method for the synthesis of a series of novel β-acylamino furans stating from renewable monosaccharide was achieved. Glucosamine hydrochloride was selectively N-acylated with acyl chlorides in methanol/triethylamine to yield N-acyl-d -glucosamines, which were subsequently converted into β-a...

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Published inJournal of carbohydrate chemistry Vol. 39; no. 9; pp. 472 - 484
Main Authors Cao, Zhi-ling, Zhu, Cong, Wu, Wen-ying, Zhu, Dan-dan, Qian, Dong, Zhu, Jian, Chang, Tian-ge, Sheng, Mei, Yang, Xiu-li, Liu, Wei-wei
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis 21.11.2020
Taylor & Francis Ltd
Subjects
acylation
amino furan
Biochemistry & Molecular Biology
Chemistry
Chemistry, Organic
Dehydration
Furans
Glucosamine
Life Sciences & Biomedicine
Monosaccharides
Physical Sciences
Science & Technology
Synthesis
Triethylamine
synthesis
Glucosamine
ACID
CONVERSION
dehydration
amino furan
acylation
DERIVATIVES
CELLULOSE
ACETYL-D-GLUCOSAMINE
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Summary:A facile method for the synthesis of a series of novel β-acylamino furans stating from renewable monosaccharide was achieved. Glucosamine hydrochloride was selectively N-acylated with acyl chlorides in methanol/triethylamine to yield N-acyl-d -glucosamines, which were subsequently converted into β-acylamino furans through dehydration and cyclization under microwave irradiation.
ISSN:0732-8303
1532-2327
DOI:10.1080/07328303.2021.1895195