Author:
Baer Hans H.,Rank Werner,Kienzle Frank
Abstract
Starting from methyl 3-deoxy-3-nitro-β-D-glucopyranoside (1), the free sugar 3-deoxy-3-nitro-α-D-glucopyranose (2), its tetraacetate (3), and 2,4,6-tri-O-acetyl-3-deoxy-3-nitro-α-D-glucopyranosyl bromide (4) were prepared. Another sequence of reactions commencing with 1 gave the 6-O-trityl (6), the 2,4-di-O-acetyl-6-O-trityl (7), the 2,4,6-tri-O-acetyl (8), and the 2,6-di-O-acetyl (10) derivatives of 1, whereas the 2,4-di-O-acetyl derivative (9) could not be isolated in pure form because of acetyl group migration. Reaction of the bromide 4 with water, methanol, and benzyl alcohol, respectively, led to 2,4,6-tri-O-acetyl-3-deoxy-3-nitro-β-D-glucopyranose (5) and the corresponding methyl and benzyl β-D-glycosides (8 and 11). Condensation of 4 with 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose (12), and condensation of tetra-O-acetyl-α-D-glucopyranosyl bromide (14) with the trityl compound 6, furnished derivatives of gentiobiose having a deoxynitro function at C-3′ (13) and C-3 (15), respectively.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
25 articles.
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