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De Novo Synthesis of Racemic 4‐Deoxy‐4,4‐difluoro‐ and 2,4‐Dideoxy‐2,4,4‐trifluorohexosides
Author(s) -
Giuffredi Guy T.,
Bernet Bruno,
Gouverneur Véronique
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100565
Subject(s) - chemistry , yield (engineering) , stereochemistry , glycal , organic chemistry , combinatorial chemistry , stereoselectivity , catalysis , materials science , metallurgy
A range of racemic 4‐deoxy‐4,4‐difluorinated carbohydrates were prepared by using a diversity‐oriented de novo synthesis starting with three commercially available two‐carbon building blocks. A common gem ‐difluorinated glycal was prepared in 35 % yield in seven steps, from which five different 4‐deoxy‐4,4‐difluoro‐ and 4‐deoxy‐2,4,4‐trifluorohexopyranosides were accessed using well‐established functional group manipulations.