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Pyrrolopyrimidine nucleosides II. the total synthesis of 7‐ β ‐D‐ribofuranosylpyrrolo[2,3‐ d ]pyrimidines related to toyocamycin
Author(s) -
Tolman Richard L.,
Robins Roland K.,
Townsend Leroy B.
Publication year - 1967
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.5570040211
Subject(s) - chemistry , pyrimidine , stereochemistry , nucleoside , derivative (finance) , anomer , economics , financial economics
The first synthesis of a 7‐β‐D‐ribofuranosylpyrrolo[2,3‐ d ]pyrimidine by direct ribosidation of a preformed pyrrolo[2,3‐ d ]pyrimidine has now been accomplished via the fusion procedure. Subsequent functional group transformations furnished the 6‐methyl‐thio derivative of the nucleoside antibiotic toyocamycin. Preparation of the 1‐, 3‐ and 7‐methyl isomers of 4‐amino‐5‐cyano‐6‐methylthiopyrrolo[2,3‐ d ]pyrimidine was accomplished and has provided an unequivocal assignment for the actual site of ribosidation by a comparison of ultraviolet absorption spectra. Factors utilized for the assignment of anomeric configuration are discussed.