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A Practical Access to 1,2‐Diaminophytosphingolipids
Author(s) -
Harrak Youssef,
Llebaria Amadeu,
Delgado Antonio
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800565
Subject(s) - chemistry , regioselectivity , acylation , amine gas treating , primary (astronomy) , combinatorial chemistry , ring (chemistry) , organic chemistry , catalysis , physics , astronomy
A practical approach to the synthesis of phytosphingolipids containing the 1,2‐diamino framework is described. The methodology relies on the regioselective ring‐opening of phytosphingosine‐derived N ‐nosylaziridines 4 and 6 with primary or secondary amines, acylation and subsequent deprotection steps. For practical purposes, N ‐substituted benzylamines were used as protected primary amine surrogates to avoid side‐reactions in the course of the N ‐nosyl deprotection step.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)