Studies on the Regioselective Reductive Ringcleavage Reactions of 3,5-O-Arylidene- d-xylofuranosides

Abstract

Reductive ring cleavage of 3,5-O-arylidene-d-xylofuranosides using LiA1H₄–A1C1₃ and NaBH₃CN–BF₃ proceeded regioselectively to provide secondary alcohol as the major product. The effect of the substitutents on the selectivity is examined.

Keywords:

• Regioselective reductive cleavage
• Xylofuranosides
• Benzylidene ketals
• Projective groups
• Hydride reducing agents

Acknowledgment

We thank the National Science Council of the Republic of China for the Financial support. (NSC 85-2113-M-230-0027). We also thank our research students—Li-Wen Wang, Ti-Chung Huang, and Hsiao-Ting Huang.