On the possibility of determining stereochemistry in acyclic polyhydroxylated compounds by the combined vicinal coupling constant/molecular mechanics method. A test with alditol peracetates
Relative configurations of multiple asymmetric centers in alditol peracetates can be determined with 92% confidence from vicinal H/H coupling constants along backbone chain and molecular mechanics calculations.
A Stereochemically General Synthesis of 2-Deoxyhexoses via the Asymmetric Allylboration of 2,3-Epoxy Aldehydes
A stereochemically general strategy for the synthesis of 2-deoxyhexoses is described.This new approach involves the asymmetric allylboration of epoxy aldehydes 12 and 13, prepared via the Sharpless asymmetric epoxidation reaction, as a means of establishi
Roush, William R.,Straub, Julie A.,VanNieuwenhze, Michael S.
p. 1636 - 1648
(2007/10/02)
D-GLUCOPYRANOSYL PHENYLSULFONES: THEIR USE IN A STEREOCONTROLLED SYNTHESIS OF CIS 2,6-DISUBSTITUTED TETRAHYDROPYRANS (β-D-C-GLYCOSIDES)
The lithiated anion derived from 3,4,6-tri-O-t-butyldimethylsilyl-2-deoxy-α,β-D-glucopyranosyl phenylsulfones 1 reacts with various electrophiles leading to alkylated products, precursors of β-D-C-glycosides 5a-g after stereocontrolled desulfonylation and
Beau, Jean-Marie,Sinay, Pierre
p. 6189 - 6192
(2007/10/02)
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