Direct Syntheses of Methyl 2-Deoxy-2-alkoxycarbonylamino-D-glucopyranoside from 2-Amino-2-deoxy-D-glucose
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Methyl 2-acetamido-2-deoxy-β-D-glucopyranoside dihydrate and methyl 2-formamido-2-deoxy-β-D-glucopyranoside.
Methyl 2-acetamido-2-deoxy-β-D-glucopyranoside (β-GlcNAcOCH(3)), (I), crystallizes from water as a dihydrate, C(9)H(17)NO(6)·H(2)O, containing two independent molecules [denoted (IA) and (IB)] in the asymmetric unit, whereas the crystal structure of methyl 2-formamido-2-deoxy-β-D-glucopyranoside (β-GlcNFmOCH(3)), (II), C(8)H(15)NO(6), also obtained from water, is devoid of solvent water molecul...
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Efficient syntheses of three [C]methyl 2-[N]amino-2-deoxy-D-glucopyranoside derivatives are described. Amination of the D-glucal with (saltmen)Mn(N) proceeded with 11:1 stereoselectivity favoring the gluco configuration; subsequent methylation of the [N]lactol using [C]iodomethane and silver(I) oxide afforded the doubly labeled glucoside in high yield. This compound served as the common precurs...
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ژورنال
عنوان ژورنال: Bulletin of the Chemical Society of Japan
سال: 1974
ISSN: 0009-2673,1348-0634
DOI: 10.1246/bcsj.47.781