Metal trifluoromethanesulfonate-catalyzed regioselective borane-reductive ring opening of benzylidene acetals: a concise synthesis of 1,4-dideoxy-1,4-imino-L-xylitol.
[reaction: see text] A highly regioselective borane-reductive ring opening of the 4,6-O-benzylidene-D-hexopyranosides to the corresponding 6-alcohols in excellent yields at room temperature via various metal trifluoromethanesulfonates as catalysts is described here. Its application in the synthesis of 1,4-dideoxy-1,4-imino-L-xylitol is also highlighted.
Wang
Cheng-Chung
CC
Institute of Chemistry, Academia Sinica, Taipei 115, Taiwan.
Luo
Shun-Yuan
SY
Shie
Chi-Rung
CR
Hung
Shang-Cheng
SC
D000606:Amino Sugars / Q000737:chemistry; D001597:Benzylidene Compounds; D001880:Boranes / Q000737:chemistry; D002384:Catalysis; D050113:Imino Furanoses; D008698:Mesylates / Q000737:chemistry*; D014993:Xylitol / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
C467078:1,4-dideoxy-1,4-imino-xylitol; D000606:Amino Sugars; D001597:Benzylidene Compounds; D001880:Boranes; D050113:Imino Furanoses; D008698:Mesylates; C012077:trifluoromethanesulfonic acid; D014993:Xylitol