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Coupling of Unprotected 2‐Deoxy‐ D ‐ribose at C‐3 as a New Route to 2,3‐Dideoxy‐3‐phthalimido‐ D ‐pentoses
Author(s) -
Motawia Mohammed S.,
Nawwar Galal A. M.,
Andreassen Erik S.,
Jacobsen Jens Peter,
Pedersen Erik B.
Publication year - 1987
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.198719870881
Subject(s) - chemistry , acetic anhydride , pyridine , furanose , moiety , pyranose , reagent , derivative (finance) , pentose , medicinal chemistry , acetylation , trimethylsilyl trifluoromethanesulfonate , organic chemistry , stereochemistry , ring (chemistry) , financial economics , economics , catalysis , biochemistry , fermentation , gene
Direct condensation of 2‐deoxy‐ D ‐ribose ( 2 ) with phthalimides using P 4 O 10 /H 2 O/Bu 3 N reagent in chloroform at 40°C results in a coupling at C‐3 of the carbohydrate moiety to give an isomeric mixture of 2,3‐dideoxy‐3‐phthalimido‐ D ‐pentoses 3–5 . Acetylation of 3b–5b using acetic anhydride in dry pyridine gives the corresponding acetylated derivatives 6–8 . After treating the mixture of 3b, 4b , and 5b with triphenylmethyl chloride in pyridine, pure threo ‐pyranose derivative 3b and pure tritylated erythro ‐furanose derivative 9 are obtained by fractional precipitation.