An Efficient Synthesis of 2'-O-(β-D-Ribofuranosyl)biopterin

An Efficient Synthesis of 2'-O-(β-D-Ribofuranosyl)biopterin

N2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1',2'-di-O-(trimethylsilyl)biopterin (4) was prepared from biopterin (1a, 86% overall yield) in 5 steps. Glycosylation of 4 with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (5a) and its 2,3,5-tri-O-benzoyl analog (5b) respectively affo...

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Bibliographic Details
Main Authors: Hanaya Tadashi, Torigoe Kiyoshi, Soranaka Kazuyuki, Fujita Hiroshi, Pfleiderer Wolfgang, Yamamoto Hiroshi
Format: Article
Language:English
Published: De Gruyter 2008-02-01
Series:Pteridines
Subjects:
biopterin d-riboside
pterin glycoside
glycosylation
protecting groups
Online Access:https://doi.org/10.1515/pteridines.2008.19.1.72
Description
Summary:N2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1',2'-di-O-(trimethylsilyl)biopterin (4) was prepared from biopterin (1a, 86% overall yield) in 5 steps. Glycosylation of 4 with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (5a) and its 2,3,5-tri-O-benzoyl analog (5b) respectively afforded the corresponding 2'-O-(2,3,5-tri-Oacetyl- and 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)biopterin derivatives (6a, 42% and 6b, 60%) as major products. Removal of the protecting groups of 6b provided 2'-O-(β-D-ribofuranosyl)biopterin (1c, 87% overall yield) in 3 steps.
ISSN:0933-4807
2195-4720

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