The formation of branched-chain deoxypentofuranosides by ring contraction in the reductive desulfonyloxylation of hexopyranoside p-toluenesulfonates

…, DJ Astles, HC Chin, L Siemsen

Index: Baer, Hans H.; Astles, David J.; Chin, Ho-chi; Siemsen, Lisa Canadian Journal of Chemistry, 1985 , vol. 63, p. 432 - 439

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Citation Number: 17

Abstract

Several methyl 6-deoxy-, 6-deoxy-6-halo-, and 6-Op-tolylsulfonylhexopyranoside 2-and 4-p- toluenesulfonates reacted readily with lithium triethylborohydride in boiling tetrahydrofuran under reductive desulfonyloxylation at C-2 and C-4, respectively, and with reduction at C-6 where applicable. The desulfonyloxylations proceeded with ring contraction to furnish, in 40- 60% isolated yields, new branched-chain pentofuranoside derivatives, namely, methyl 2, ...