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.

Paper | Special issue | Vol 79, No. 1, 2009, pp.967-983
Published online, 7th January, 2009
DOI: 10.3987/COM-08-S(D)74
Tandem Catalysis Strategy for Direct Glycosylation of 1-Hydroxy Sugars. Methoxyacetic Acid as an Effective Catalytic Mediator

Yasuo Yokoyama,* Takeshi Hanamoto, Shoko Suzuki, Kosuke Shimizu, Hiroshi Furuno, and Junji Inanaga*

*Akita National College of Technology, Iijima-bunkyomachi 1-1, Akita, Akita 011-0923, Japan


1-Hydroxy sugars were dehydratively coupled with a variety of alcohols including thiophenol in the presence of a catalytic amount of ytterbium(III) triflate [Yb(OTf)3] and methoxyacetic acid to give the corresponding glycosides in good to excellent yields, and in some cases, with high stereoselectivities. The reaction proceeds through selective esterification of 1-hydroxy sugars with methoxyacetic acid in the presence of free alcohols as glycosyl acceptors. The mechanism of methoxyacetic acid-mediated tandem catalysis with Yb(OTf)3 is discussed.