Synthesis and Conformational Analysis of 6-C-Methyl-Substituted 2-Acetamido-2-deoxy-β-d-glucopyranosyl Mono- and Disaccharides
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چکیده
منابع مشابه
Synthesis and conformational analysis of 6-C-methyl-substituted 2-acetamido-2-deoxy-beta-D-glucopyranosyl mono- and disaccharides.
Several 6-C-substituted 2-acetamido-2-deoxy-beta-D-glucopyranosides (beta-D-GlcNAc monosaccharides 1a-3a and 1,4-linked disaccharides 1b-3b) were studied by solution NMR spectroscopy. Conformational analysis of the (6S)- and (6R)-C-methyl-substituted beta-d-GlcNAc monosaccharides indicates that the stereodefined methyl groups impose predictable conformational biases on the exocyclic C-5-C-6 bon...
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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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The 2-mono and 2,6-disubstituted methyl-1,4-dihydropyridines were synthesized by reaction of morpholine, thiophenol, 8-hydroxyquinoline, 2-naphthol and 2-mercopto-1-methyl imidazole with the 2-mono bromo and 2,6-dibromo-1,4-dihidropyridines.
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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...
متن کاملFacile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranosides from ManNAc-oxazoline
The synthetic procedures for a large-scale preparation of o- and p-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside are described. The synthetic pathway employs the glycosylation of phenol with ManNAc oxazoline, followed by nitration of the aromatic moiety yielding a separable mixture of the o- and p-nitrophenyl derivative in a 2:3 ratio.
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ژورنال
عنوان ژورنال: The Journal of Organic Chemistry
سال: 2005
ISSN: 0022-3263,1520-6904
DOI: 10.1021/jo0485841