Open AccessFirst Synthesis of Biopterin α-D-Glucoside
Author(s) -
Tadashi Hanaya,
Hiroki Baba,
Hiroshi Yamamoto
Publication year - 2009
Publication title -
heterocycles
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.242
H-Index - 64
eISSN - 1881-0942
pISSN - 0385-5414
DOI - 10.3987/com-08-s(f)60
Subject(s) - biopterin , chemistry , pterin , tetramethylurea , cyanobacteria , bacteria , glycoside , glycosidic bond , stereochemistry , rhamnose , glucoside , biochemistry , polysaccharide , cofactor , biology , solvent , tetrahydrobiopterin , medicine , alternative medicine , pathology , enzyme , genetics
A novel glycosyl donor, 4,6-di-O-acetyl-2,3-di-O-(4-methoxy-benzyl)-α-D-glucopyranosy bromide (15) was efficiently prepared from D-glucose in 8 steps. The first synthesis of 2’-O-(α-D-glucopyranosyl)biopterin (2) was achieved by treatment of the key precursor, N(2)-(N,N-dimethylamino- methylene)-1’-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (6) with 15 in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups
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