Syntheses of C- and N-nucleosides from 1-aza-2-azoniaallene and 1,3-diaza-2-azoniaallene salts

被引：47

作者：

Al-Masoudi, N ^{[1
]}

Hassan, NA ^{[1
]}

Al-Soud, YA ^{[1
]}

Schmidt, P ^{[1
]}

Gaafar, AEDM ^{[1
]}

Weng, M ^{[1
]}

Marino, S ^{[1
]}

Schoch, A ^{[1
]}

Amer, A ^{[1
]}

Jochims, JC ^{[1
]}

机构：

[1] Univ Konstanz, Fak Chem, D-78434 Constance, Germany

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 05期

关键词：

D O I：

10.1039/a707079i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

C-Nucleosides are prepared by cycloaddition of 1-aza-2-azoniaallene salts 2 and 1,3 -diaza-2-azoniaallene salts 5 to the triple bonds of a glycosylalkyne and of glycosyl cyanides, Thus, the glucosylalkyne 7 reacts with salts 5 to give the 4-glucosyl-1,2,3-triazolium salt 8, From the galactosyl cyanide 9, the ribofuranosyl cyanide 13, and several 1-aza-2-azoniaallene salts 2 the glycosyl-1,2,4-triazoles 11, 15, 17 are obtained, Deacylation affords the free C-nucleosides 12, 16, 18, Cycloaddition to the C=S double bond of the glucosyl isothiocyanate 19 furnishes glucosylimino-1,3,4-thiaziazoles 20-22. A new method for the preparation of the isothiocyanate 19 is described.

引用

页码：947 / 953

页数：7

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