An efficient stereoselective synthesis of the amino sugar component (E ring) of calicheamicin γ 1 I

…, V Di Bussolo, L Favero, F Macchia, M Pineschi

Index: Crotti; Di Bussolo; Favero; Macchia; Pineschi Tetrahedron Asymmetry, 1996 , vol. 7, # 3 p. 779 - 786

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Citation Number: 17

Abstract

A simple, efficient, stereoselective synthesis of the methyl 2, 4-dideoxy-4-(ethylamino)-3-O- methyl-β-L-threo-pentopyranoside2, corresponding to the E monosac-charide unit (E ring) of calicheamicin 1, is described. The synthetic procedure utilizes the methyl 2-deoxy-β-D- ribopyranoside 3 as the enantiopure starting material and the acid methanolysis of the intermediate activated aziridine 12 to give the desired amino sugar 2 in 6 steps and in ...

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