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Exploration of Routes Leading to Derivatives of α‐Hydroxyalanine and its Precursors
Author(s) -
Liwschitz Y.,
Singerman A.,
Wiesel Y.,
Michman M.,
Braun P.,
Kassel S. Hananel,
Perera D.
Publication year - 1971
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.197100017
Subject(s) - chemistry , benzyl alcohol , polymerization , organic chemistry , protecting group , molecule , combinatorial chemistry , polymer , catalysis , alkyl
The preparation of fully protected derivatives of DL‐α‐hydroxyalanine is described. Several possible routes leading to protected DL‐α‐hydroxyalanine and α‐hydroxyglycine were explored. Attempts to remove the protecting groups led in most cases to the disruption of the molecule. The N‐carboxyanhydride of O‐benzyl‐DL‐α‐hydroxyalanine was prepared and trimerised to give dehydroalanyl‐O‐benzyl‐DL‐α‐hydroxyalanyldehydroalanine. This is a novel type of polymerization of N‐carboxyanhydrides concurrent with elimination of benzyl alcohol. A generally useful method of purification of oily half esters of dicarboxylic acids through their crystalline dibenzylamine salts has been developed.