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 |
Keywords
- Biopterine d-Glucoside
- Protecting Group
- Pteridine
- Pterine Glycoside
- Selective α-Glycosylation
ASJC Scopus subject areas
- Analytical Chemistry
- Pharmacology
- Organic Chemistry
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Cite this
Hanaya, T., Baba, H., & Yamamoto, H. (2009). First synthesis of biopterin α-D-glucoside. Heterocycles, 77(2), 747-753. https://doi.org/10.3987/COM-08-S(F)60