Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Communication | Special issue | Vol 93, No. 1, 2016, pp.55-61
Published online, 16th October, 2015
DOI: 10.3987/COM-15-S(T)39
Stereoselectivity of D-Psicofuranosylation Influenced by Protecting Groups of Psicofuranosyl Donors

Takashi Yamanoi,* Yoshiki Oda, Toshiaki Ishiyama, and Mikio Watanabe

*Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan


We synthesized several types of novel D-psicofuranosyl acetate derivatives, and investigated their use as glycosyl donors in scandium triflate-catalyzed D-psicofuranosylation reactions. Psicofuranosylation demonstrated unique stereoselectivities depending on the protecting groups of psicofuranosyl donors. The donor having a 3,4-isopropylidene group afforded β-psicofuranosides with high stereoselectivities. Donors having a C3 benzoyloxy group demonstrated low stereoselectivities with no neighboring group participation. This study also discusses the stereoselectivities of psicofuranosylation based on the conformers of the glycosyl oxocarbenium ion intermediates as influenced by the protecting groups of the psicofuranosyl donors. We also compared the neighboring group participation of the glycosyl donors bearing a C3 benzoyloxy group during D-psicofuranosylation and D-fructofuranosylation.