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Solid Phase Synthesis of 4″‐ epi ‐Methylamino‐4″‐deoxyavermectin B 1 Benzoate
Author(s) -
MingKun Fu,
Xian Wu,
Jun Ning,
JianZhong Li
Publication year - 2005
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200590901
Subject(s) - chemistry , hydroxymethyl , solid phase synthesis , amination , silylation , cleavage (geology) , polystyrene , reductive amination , benzoyl chloride , organic chemistry , stereochemistry , catalysis , biochemistry , peptide , fracture (geology) , engineering , polymer , geotechnical engineering
To implement the solid phase synthesis of 4″‐ epi ‐methylamino‐4″‐deoxyavermectin B 1 benzoate, tert ‐butyl‐ dimethylsilylchloride was chosen for the first solution synthesis. Then a novel silyl chloride resin 1 , achieved from hydroxymethyl polystyrene resin and dimethyldichlorosilane, was used successfully for the attachment of avermectin B 1 2 . Through oxidation, amination formation, cleavage, and benzoate formation, resin bounded avermectin B 1 9 gave 4″‐ epi ‐methylamino‐4″‐deoxyavermectin B 1 benzoate 6 .