Abstract
A novel glycosyl donor, 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-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, N2-(N,N- dimethylaminomethylene)-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.
| Original language | English |
|---|---|
| Pages (from-to) | 747-753 |
| Number of pages | 7 |
| Journal | Heterocycles |
| Volume | 77 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - Feb 1 2009 |
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Keywords
- Biopterine d-Glucoside
- Protecting Group
- Pteridine
- Pterine Glycoside
- Selective α-Glycosylation
ASJC Scopus subject areas
- Analytical Chemistry
- Organic Chemistry
- Pharmacology
Cite this
First synthesis of biopterin α-D-glucoside. / Hanaya, Tadashi; Baba, Hiroki; Yamamoto, Hiroshi.
In: Heterocycles, Vol. 77, No. 2, 01.02.2009, p. 747-753.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - First synthesis of biopterin α-D-glucoside
AU - Hanaya, Tadashi
AU - Baba, Hiroki
AU - Yamamoto, Hiroshi
PY - 2009/2/1
Y1 - 2009/2/1
N2 - A novel glycosyl donor, 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-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, N2-(N,N- dimethylaminomethylene)-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.
AB - A novel glycosyl donor, 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-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, N2-(N,N- dimethylaminomethylene)-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.
KW - Biopterine d-Glucoside
KW - Protecting Group
KW - Pteridine
KW - Pterine Glycoside
KW - Selective α-Glycosylation
UR - http://www.scopus.com/inward/record.url?scp=68549089860&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=68549089860&partnerID=8YFLogxK
U2 - 10.3987/COM-08-S(F)60
DO - 10.3987/COM-08-S(F)60
M3 - Article
AN - SCOPUS:68549089860
VL - 77
SP - 747
EP - 753
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 2
ER -