Stereoselective Synthesis of β-Glucosides with l, l′-Diacetal Structure

Authors

  • Prof. Dr. Lutz-F. Tietze,

    Corresponding author
    1. Organisch-chemisches Institut der Universitat, Tammannstrasse 2. D-3400 Göttingen (Germany)
    • Organisch-chemischcs Inslilul der Universiiat Tammannslrassc 2. D-3400 Goitingcn (Germany)
    Search for more papers by this author
  • Dipl.-Chem. Roland Fischer

    1. Organisch-chemisches Institut der Universitat, Tammannstrasse 2. D-3400 Göttingen (Germany)
    Search for more papers by this author

  • This work was supported by the Fonds der Chemischen Industrie.

  • Dedicated to Professor George Büchi on the occasion of his 60th birthday

Abstract

original image

An example of the use of trimethylsilyl trifluoromethanesulfonate as catalyst is the reaction of β-D-glucopyranoside (1) with acetals (R1 = Me, Ph; R2 = H, CH2Ph, n-C3H7, CH2CH(OMe)2, CH2OMe etc.). It leads highly stereoselectively to the l,l′-diacetals (2) in good yields.

Ancillary