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ID 44365
フルテキストURL
著者
Hanaya, Tadashi Department of Chemistry, Faculty of Science, Okayama University
Baba, Hiroki Department of Chemistry, Faculty of Science, Okayama University
Toyota, Hiroki Department of Chemistry, Faculty of Science, Okayama University
Yamamoto, Hiroshi School of Pharmacy, Shujitsu University
抄録
L-Rhamnose was led, in a 14-step-sequence, to N2-(N,N-dimethylaminomethylene)-1′-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (23), an appropriately protected precursor for 2′-O-glycosylation, while 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-α-d-glucopyranosyl bromide (32), a novel glycosyl donor, was efficiently prepared from d-glucose in 8 steps. The first synthesis of 2′-O-(α-d-glucopyranosyl)biopterin (2a) was achieved by treatment of the key intermediate 23 with 32 in the presence of silver triflate and tetramethylurea, followed by successive removal of the protecting groups.
キーワード
Pterin glycoside
Pteridine
Glycosylation
Protecting group
Total synthesis
発行日
2009-09-19
出版物タイトル
Tetrahedron
65巻
38号
出版者
Pergamon-Elsevier Science Ltd.
開始ページ
7989
終了ページ
7997
ISSN
0040-4020
NCID
AA00861787
資料タイプ
学術雑誌論文
オフィシャル URL
http://dx.doi.org/10.1016/j.tet.2009.07.043
言語
English
著作権者
Copyright © 2009 Elsevier Ltd All rights reserved.
論文のバージョン
author
査読
有り
DOI
Web of Science KeyUT