期刊
JOURNAL OF CARBOHYDRATE CHEMISTRY
卷 26, 期 5-6, 页码 279-303出版社
TAYLOR & FRANCIS INC
DOI: 10.1080/07328300701540183
关键词
D-glucosamine propane-1,3-diyl dithioacetal; protecting group; selective protection
D-glucosamine propane-1,3-diyl dithioacetal is a versatile synthetic building block, especially when being incorporated with the Corey-Seebach method. Hence, exploring compatible protecting group patterns on this compound mainly for use with the Corey-Seebach method is a fundamental work. Various protecting group strategies were applied. Typically, N- protection of D- glucosamine propane- 1,3- diyl dithioacetal yielded N- phthaloyl, N-Boc, and N-Ac derivatives. On the N-Ac derivative, experiments differentiating 3,4- and 5,6- hydroxyls by basic stable protecting groups yielded useful intermediates. Selective protections of the 6- hydroxyl of the N-Ac derivative were also applied. The remaining secondary hydroxyls of the resulting N-Ac-6-O- acyl D- glucosamine propane-1,3- diyl dithioacetals could be methoxymethylated to tri-O-MOM derivatives or protected by a unique one- pot discriminating protection to form the N-acyl-6-O-acyl-3,4-O-methylene-5- O-methoxymethyl D-glucosamine propane-1,3-diyl dithioacetals as useful intermediates.
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