@article{b34f50ffe6a449849b1f1a8ba7fc2095,
title = "1,2-trans Glycosylation via Neighboring Group Participation of 2- O-Alkoxymethyl Groups: Application to One-Pot Oligosaccharide Synthesis",
abstract = "The use of 2-O-alkoxymethyl groups as effective stereodirecting substituents for the construction of 1,2-trans glycosidic linkages is reported. The observed stereoselectivity arises from the intramolecular formation of a five-membered cyclic architecture between the 2-O-alkoxymethyl substituent and the oxocarbenium ion, which provides the expected facial selectivity. Furthermore, the observed stereocontrol and the extremely high reactivity of 2-O-alkoxymethyl-protected donors allowed development of a one-pot sequential glycosylation strategy that should become a powerful tool for the assembly of oligosaccharides.",
author = "Milandip Karak and Yohei Joh and Masahiko Suenaga and Tohru Oishi and Kohei Torikai",
note = "Funding Information: This work was supported by JSPS KAKENHI (Grant Nos. JP15K21210, JP18K05462) and grants from the Heiwa Nakajima Foundation (Japan) and the Nakamura Jishiro Ikueikai Foundation (Japan) to K.T. M.K. thanks Heiwa Nakajima Foundation (Japan) and Takeda Science Foundation (Japan) for research fellowships. We are grateful to Mr. Takaaki Torikai, Ms. Rumiko Torikai, Mr. Motoaki Yamaoka, Ms. Michie Yamaoka, Ms. Kimiko Komiya, and Dr. Kazuhiro Matsunaga for their generous personal financial donations. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",
year = "2019",
month = feb,
day = "15",
doi = "10.1021/acs.orglett.9b00220",
language = "English",
volume = "21",
pages = "1221--1225",
journal = "Organic letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "4",
}