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Novel stereoselective synthesis of 1-(β-d- and α-l-glycopyranosyl)-5-methyl-1H-1,2,4-triazoles

✍ Scribed by Jianxin Yu; Zhongjun Li; Wenjie Lu; Suna Zhang; Mengshen Cai

Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 204 KB
Volume: 14
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(03)00491-9

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✦ Synopsis

1-(b-D

-and a-L-Glycopyranosyl)-5-methyl-1H-1,2,4-triazoles 7, 13-15 were synthesized stereoselectively from the corresponding glycopyranosyl aminoguanidine nitrates 1-3 in boiling acetic anhydride or from N 1 -(acetylated b-Dor a-Lglycopyranosylamino)-N 1 ,N 2 ,N 3 -triacetylguanidines 8-10 using catalytic amounts of NaOMe. Structures were confirmed by elemental analyses, IR, NMR and MS and possible mechanisms are discussed. In vitro antitumor and immuno activities are presented.

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