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ID 44365
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Author
Baba, Hiroki
Toyota, Hiroki
Yamamoto, Hiroshi
Abstract
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.
Keywords
Pterin glycoside
Pteridine
Glycosylation
Protecting group
Total synthesis
Published Date
2009-09-19
Publication Title
Tetrahedron
Volume
volume65
Issue
issue38
Publisher
Pergamon-Elsevier Science Ltd.
Start Page
7989
End Page
7997
ISSN
0040-4020
NCID
AA00861787
Content Type
Journal Article
Official Url
http://dx.doi.org/10.1016/j.tet.2009.07.043
language
英語
Copyright Holders
Copyright © 2009 Elsevier Ltd All rights reserved.
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author
Refereed
True
DOI
Web of Sience KeyUT