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The synthesis of some purine nucleosides from 4,6‐di‐ O ‐acetyl‐3‐deoxy‐3‐(ethoxycarbonylamino)‐ D ‐glucal
Author(s) -
Lourens Gerhardus J.,
Jordaan A.
Publication year - 1972
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.5570090501
Subject(s) - chemistry , glucal , dimethylamine , anomer , purine , acetylation , mutarotation , stereochemistry , glycal , organic chemistry , catalysis , biochemistry , stereoselectivity , gene , enzyme
The acid catalyzed reaction of 4,6‐di‐ O ‐acetyl‐3‐deoxy‐3‐(ethoxycarbonylamino)‐D‐glucal and 6‐chloropurine in nitrometliane solution gave 6‐ehloro‐9‐(4′,6′‐di‐ O ‐acetyl‐2′,3′‐dideoxy‐3′‐ethoxy‐carbonylamino‐ α‐ and β‐D‐ arafemo hexopyranosyl)purine. These were converted to the corresponding deblocked 6‐dimetliylaminopurine nucleosides by treatment with ethanolic dimethylamine; acetylation of these gave the respective 4′,6′‐di‐ O ‐acetyl derivatives. The anomeric assignments for the nucleosides were based on their nmr spectral data.