由糖基异硫氰酸酯简便合成1,2,4-三唑和均三嗪糖苷。
Facile syntheses of 1,2,4-triazole and s-triazine glycosides from glycosyl isothiocyanates.
作者信息
Ogura H, Takahashi H, Sato O
出版信息
Nucleic Acids Symp Ser. 1979(6):s13-6.
PMID:547228
Abstract
Reaction of glycosyl isothiocyanates (la, b or c) with acyl or aroyl hydrazine gave the corresponding glycosyl thiosemicarbazides, and which were treated with Ac2O-H3PO4 to yield 1,2,4-triazole glycosides. Similar treatment of la, b or c with amidino compounds gave glycosylisothiobiurets, followed by N-bromosuccinimide (NBS) oxidation to give 1,2,4-triazole glycosides. Treatment of glycosylisothiobiurets with triethyl orthoformate gave the corresponding s-triazine glycosides.
摘要
异硫氰酸糖基酯（1a、b或c）与酰肼或芳酰肼反应生成相应的糖基硫代氨基脲，然后用乙酸酐-磷酸处理得到1,2,4-三唑糖苷。1a、b或c与脒类化合物进行类似处理得到糖基异硫代双缩脲，接着用N-溴代琥珀酰亚胺（NBS）氧化得到1,2,4-三唑糖苷。糖基异硫代双缩脲与原甲酸三乙酯反应得到相应的均三嗪糖苷。
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