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