Studies on D-Glucosamine Derivatives. VI. α-1-C-Phenyl-2-acetamido-2-deoxy-D-glucopyranoside and its Derivatives
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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...
متن کاملStereoselective synthesis of [C]methyl 2-[N]amino-2-deoxy- -D-glucopyranoside derivatives
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 کاملSome further studies on the synthesis of glycopeptide derivatives: 2-acetamido-2-deoxy-beta-D-glucopyranosylamine derivatives.
1. The isolation, characterization and properties of two by-products in the preparation of 2-acetamido-3,4,6-tri-O- acetyl-2-deoxy-beta-d-glucopyranosylamine are described. They are bis(2-acetamido-2-deoxy-d-glucopyranosyl)amines. 2. An independent synthesis of the bis-glycopyranosylamines is reported and conditions are given for their preparation in high yield. 3. Further improvements are give...
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Diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside is a synthetic saponin exhibiting attractive pharmacological properties. Different pathways tested by us to obtain this glycoside are summarized here. Moreover, the synthesis of N-alkyl and N,N-dialkyl derivatives of the glucopyranoside is presented. Evaluation of antibacterial and antifungal activities of these derivatives indicates that they have ...
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: Bulletin of the Chemical Society of Japan
سال: 1961
ISSN: 0009-2673,1348-0634
DOI: 10.1246/bcsj.34.8