67596-51-4Relevant academic research and scientific papers
Iridoids, XXII. - Glucosidation of Hemiacetals. - Highly Stereoselective Synthesis of Iridoid Glucosides
Tietze, Lutz F.,Fischer, Roland,Remberg, Gerd
, p. 971 - 976 (2007/10/02)
Reaction of the racemic iridoid aglucone acetates 9d-12d with the trimethylsilyl β-glucopyranoside 4a in the presence of catalytic amounts of trimethylsilyl trifluoromethanesulfonate (7) in acetonitrile or liquid sulfur dioxide at -30 deg C and -50 deg C, respectively, followed by solvolysis gives in excellent yields nearly exclusively the β-glucosides 9g and 11g.Glucosidation of the enantiomerically pure acetates 9d/10d affords the β-glucoside 9g.In a similar way, the biosynthetical key intermediate loganin (1) is obtained from 16a in 60 percent yield.
