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Syntheses of thymidine diphosphoglucose derivatives
Author(s) -
Liemann Susanne,
Klaffke Werner
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199510249
Subject(s) - chemistry , anomer , glycosyl , yield (engineering) , derivative (finance) , phosphate , combinatorial chemistry , stereochemistry , organic chemistry , materials science , economics , financial economics , metallurgy
Per‐ O ‐benzoylated 3‐ and 4‐deoxy‐α‐ D ‐glucopyranoses 3 and 12 , as well as the respective 4‐isobutyramido derivative 29 were converted into their hemiacetals, phosphitylated, and oxidized to yield anomeric mixtures of glycosyl phosphates. These partially esterified compounds were coupled with dTMP morpholidate to give after complete deblocking dTDP‐3‐deoxy‐α‐ D ‐glucose ( 11 ), dTDP‐4‐deoxy‐α‐ D ‐glucose ( 19 ) and dTDP‐4‐amino‐4‐deoxy‐α‐ D ‐glucose ( 36 ). 3‐Acetamido‐3‐deoxy‐α‐ D ‐glucopyranosyl phosphate was synthesized according to the silver diphenyl phosphate procedure and subsequently converted into dTDP‐3‐acetamido‐3‐deoxy‐α‐ D ‐glucose (dTDP‐ N ‐acetyl‐ D ‐kanosamine) ( 26 ) by hydrogenation and coupling with dTMP morpholidate.