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Synthesis of (2′ S )‐2′‐Deoxy‐2′‐ C ‐methylpurine Nucleosides and Their Phosphoramidites
Author(s) -
Caballero Gerardo,
Gallo Mariana,
Montserrat Javier M.,
Iribarren Adolfo M.
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200205)85:5<1284::aid-hlca1284>3.0.co;2-s
Subject(s) - chemistry , moiety , stereoselectivity , stereochemistry , inosine , alcohol , wittig reaction , protecting group , regioselectivity , methyl group , primary alcohol , group (periodic table) , organic chemistry , catalysis , enzyme , alkyl
We describe the stereoselective synthesis of (2′ S )‐2′‐deoxy‐2′‐ C ‐methyladenosine ( 12 ) and (2′ S )‐2′‐deoxy‐2′‐ C ‐methylinosine ( 14 ) as well as their corresponding cyanoethyl phosphoramidites 16 and 19 from 6‐ O ‐(2,6‐dichlorophenyl)inosine as starting material. The methyl group at the 2′‐position was introduced via a Wittig reaction (→ 3 , Scheme 1 ) followed by a stereoselective oxidation with OsO 4 (→ 4 , Scheme 2 ). The primary‐alcohol moiety of 4 was tosylated (→ 5 ) and regioselectively reduced with NaBH 4 (→ 6 ). Subsequent reduction of the 2′‐alcohol moiety with Bu 3 SnH yielded stereoselectively the corresponding (2′ S )‐2′‐deoxy‐2′‐ C ‐methylnucleoside (→ 8a ).