Abstract
Cp 2Zr(ClO 4) 2 was used as a promoter for nucleophilic addition of 2-(trimethylsilyloxy) furan (TMSOF) to 2,3,4,6-tetra- O-benzyl- d-glucopyranosyl fluoride to give a 2:1:1 mixture of adducts in 80% yield. NMR data and postulated transition states are consistent with a 3:1 ratio of regioisomers at C-5 and C-3 of TMSOF and a 2:1 ratio of threo and erythro α-adducts at C-5.
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