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ID 34215
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Author
Baba, Hiroki
Toyota, Hiroki
Yamamoto, Hiroshi
Abstract
The key, versatile precursors N-2-(N,N-dimethylaminomethylene)-1'-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (29a) and its ciliapterin analog (29b) were prepared, respectively, from D-xylose (in 14 steps) and L-xylose (in 11 steps). Treatment of 29a and 29b with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups, led to the first selective syntheses of limipterin (3) and tepidopterin (5), respectively.
Keywords
pteridine
pterin glycoside
glycosylation
protecting group
Published Date
2008-02-25
Publication Title
Tetrahedron
Volume
volume64
Issue
issue9
Publisher
Pergamon-Elsevier Science Ltd.
Start Page
2090
End Page
2100
ISSN
0040-4020
NCID
AA00861787
Content Type
Journal Article
Official Url
http://dx.doi.org/10.1016/j.tet.2007.12.042
language
英語
Copyright Holders
Copyright © 2007 Elsevier Ltd All rights reserved.
File Version
author
Refereed
True
DOI
Web of Sience KeyUT
Submission Path
organic_chemistry/8