Chemistry of Natural Compounds p. 322 - 327 (1982)
Update date:2022-09-26
Topics:
Pozdnev, V. F.
Two variants are proposed for the synthesis of Nα-Boc-Nim-tritylhistidiine.The first variant starts from Nα,Nim-di-Boc-histidine, from which the Nim-Boc group is removed with hydrazine hydrate.The Nα-Boc-histidine formed is esterified with chlorotrimethylsilane, tritylated in the imidazole group, and, after the elimination of the trimethylsilyl protection from the carboxyl group, Nα-Boc-Nim-tritylglycine is obtained with a yield of 80percent.The second variant starts from Nα,Nim-ditritylhistidine, which, by treatment with hydrochloric acid in acetone and then with dilute ammonia, is converted into Nim- tritylhistidine.From this, by acylation with di-tert-butyl pyrocarbonate, Nα-Boc-Nim-tritylhistidine is obtained with a yield of 91percent.The acylation of Nim-tritylhistidine with other alkoxycarbonylating reagents leads to Nα-tert-amyl-, Nα-benzyl-, and Nα-4-methoxybenzyloxycarbonyl derivatives of Nim-tritylhistidine.
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Doi:10.1039/P19810001909
(1981)Doi:10.1002/ardp.19813141007
(1981)Doi:10.1016/S0040-4020(01)98969-0
(1981)Doi:10.1007/BF00503537
(1981)Doi:10.1021/jo00170a002
(1983)Doi:10.1248/cpb.29.2689
(1981)