Author:
Čapek Karel,Čapková Jindra,Jarý Jiří,Knirel Yurii A.,Shashkov Alexander S.
Abstract
Title compounds were prepared from methyl 2-O-acetyl-3,4-anhydro-6-deoxy-α-D-galactopyranoside (I). Solvolysis of I afforded methyl 3-O-acetyl-6-deoxy-α-D-gulopyranoside (II) from which in turn was prepared its 2,4-di-O-methanesulfonyl derivative III. The reaction of III with sodium azide undergoes under participation of the O-acetyl group in the position 3 and produces methyl 2,4-diazido-2,4,6-trideoxy-α-D-idopyranoside (V) that after hydrogenation and acetylation yields methyl 2,4-diacetamido-2,4,6-trideoxy-α-D-idopyranoside (VIII). Methyl 2,4-diacetamido-2,4,6-trideoxy-α-D-talopyranoside (XI) was prepared by its mesylation and by solvolysis of the product. Azidolysis of I, followed by hydrogenation and acetylation gave methyl 4-acetamido-4,6-dideoxy-α-D-glucopyranoside (XII). Its subsequent reaction with diethyl azodicarboxylate-triphenylphosphine mixture led to methyl 4-acetamido-2,3-anhydro-4,6-dideoxy-α-D-allopyranoside (XV). Mixture of methyl 4-acetamido-2-azido-2,4,6-trideoxy-α-D-altropyranoside (XVII) and its gluco- isomer XVIII is formed in the reaction of XV with sodium azide. Hydrogenation of XVII yields amino derivative XIX that in turn gives methyl 2,4-diacetamido-2,4,6-trideoxy-α-D-altropyranoside (XXI) by acetylation. Methyl 2,4-diacetamido-2,4,6-trideoxy-α-D-mannopyranoside (XXII) was prepared by its mesylation and solvolysis. All structures were confirmed by 1H and 13C NMR spectra.
Publisher
Institute of Organic Chemistry & Biochemistry
Cited by
10 articles.
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