GLYCOSIDATION ROUTE TO 4''-EPI-(METHYLAMINO)-4''-DEOXYAVERMECTIN B-1 (MK-244, EMAMECTIN BENZOATE)

Authors
LOEWE MF CVETOVICH RJ DIMICHELE LM SHUMAN RF GRABOWSKI EJJ
Citation
Mf. Loewe et al., GLYCOSIDATION ROUTE TO 4''-EPI-(METHYLAMINO)-4''-DEOXYAVERMECTIN B-1 (MK-244, EMAMECTIN BENZOATE), Journal of organic chemistry, 59(25), 1994, pp. 7870-7875
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
59
Issue
25
Year of publication
1994
Pages
7870 - 7875
Database
ISI
SICI code
0022-3263(1994)59:25<7870:GRT4B(>2.0.ZU;2-X
Abstract
A stereocontrolled glycosidation with phenyl ycarbonyl)-methylamino]-4 -deoxy-1-thiooleandroside (10) and 5-O-(allyloxycarbonyl)avermectin B- 1 monosaccharide (12) using N-iodosuccinimide gave exclusively the alp ha-anomer 13 in 90% yield. Thiophenyl oleandrose derivative 10 was pre pared from methyl oleandroside, which was prepared via methanolysis of avermectins. Deprotection and crystallization as the benzoic acid sal t gave 4''-epi-(methylamino)-4''-deoxyavermectin B-1 (1a, MK-244, emam ectin benzoate).