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Nucleocyclitols. Synthesis of substituted purinyl‐ muco ‐inositol derivatives
Author(s) -
Aguilar Guillermo J.,
Gelpi María E.,
Cadenas Raúl A.
Publication year - 1992
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570290219
Subject(s) - chemistry , triethylamine , moiety , inositol , nucleophile , purine , nucleoside , nucleophilic substitution , chlorine atom , aminocyclitol , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , biochemistry , catalysis , antibiotics , enzyme , receptor , aminoglycoside
Several carbocyclic nucleoside analogs possessing a 6‐substituted purine linked to a mesylated muco ‐inositol were synthesized. The coupling of triethylamine‐activated 6‐chloropurine with 2,3‐anhydro‐l,5,6‐tri‐ O ‐(methanesulfonyl)‐ epi ‐inositol gave a 6‐chloro purinyl muco ‐inositol amenable to further synthetic transformations in the heterocyclic moiety by substitution of the chlorine atom by nitrogen nucleophiles such as methylamino, diethylamino, benzylamino, hydrazino, morpholino, hydroxylamino, piperidino, and glycyl groups.