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Synthesis of 1 ‐[2,3‐dideoxy‐3‐(3‐hydroxypropyl)‐ D ‐pentofuranosyl]thymines
Author(s) -
Walczak Krzysztof,
Pupek Krzysztof,
Pedersen Erik B.
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1991199101179
Subject(s) - chemistry , tributyltin hydride , sodium borohydride , thymine , acrolein , derivative (finance) , radical , anomer , free radical reaction , borohydride , medicinal chemistry , radical initiator , sodium hydride , organic chemistry , catalysis , dna , biochemistry , polymer , financial economics , economics , polymerization
Free radicals generated by reaction of protected methyl 2,3‐ dideoxy‐3‐iodopentofuranosides 2, 3 , and 9 with tributyltin hydride in the presence of a radical initiator (AIBN) were treated with acrolein to give methyl 2,3‐dideoxy‐3‐(3‐oxopropyl)pentofuranosides 4 and 5 . Reduction of 5 with Sodium borohydride followed by protection of hydroxy groups by reaction with tert ‐butyl chlorodiphenylsilane gave the carbohydrate derivative 11 which was condensed with silylated thymine to afford a separable mixture of α‐ and β‐nucleosides 13 and 14 . These nucleosides were subsequently deprotected to give the 3′‐propyl‐extended thymidine 16 and its corresponding α‐isomer 15 .