250273-70-2Relevant academic research and scientific papers
Synthesis of C-mannopyranosylphloroacetophenone derivatives and their anomerization
Kumazawa, Toshihiro,Sato, Shingo,Matsuba, Shigeru,Onodera, Jun-Ichi
, p. 103 - 108 (2001)
The reaction of 2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl fluoride (6-deoxy-2,3,4-tri-O-benzyl-α-L-mannopyranosyl fluoride) with 2,4-dibenzylphloroacetophenone, in the presence of boron trifluoride·diethyl etherate, afforded both the 3-C-α-L- and the 3-C-β-L-rhamnopyranosylphloroacetophenone derivatives. The 3-C-α-L-rhamnoside was produced as a major product, while the 3-C-β-L-rhamnoside was produced as a minor product via anomerization of the 3-C-α-L-rhamnoside. Alternatively, the reaction of 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl fluoride with 2,4-di-benzylphloroacetophenone afforded both the 3-C-α-D- and the 3-C-β-D-mannnopyranosylphloroacetophenone derivatives under identical conditions. The 3-C-β-D-mannoside was produced as a major product via anomerization of the 3-C-α-D-mannoside during the reaction. These differences in composition result apparently from the magnitude of the 1,3-diaxial interactions between the C-3 and C-5 positions in these sugar moieties.
Regioselective acetyl transfer from the aglycon to the sugar in C-glycosylic compounds facilitated by silica gel
Kumazawa, Toshihiro,Akutsu, Yasuyuki,Matsuba, Shigeru,Sato, Shingo,Onodera, Jun-Ichi
, p. 129 - 137 (2007/10/03)
2'-O-Acetyl C-glycosylic compounds (C-glycosides) were prepared via regioselective acetyl transfer from aglycons to sugar moieties with silica gel in the presence of unprotected primary and secondary hydroxyl groups. Copyright (C) 1999 Elsevier Science Lt
