First synthesis of biopterin α-D-glucoside

Tadashi Hanaya; Hiroki Baba; Hiroshi Yamamoto

doi:10.3987/COM-08-S(F)60

First synthesis of biopterin α-D-glucoside

Tadashi Hanaya, Hiroki Baba, Hiroshi Yamamoto

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Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

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	https://doi.org/10.3987/COM-08-S(F)60
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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title = "First synthesis of biopterin α-D-glucoside",

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.",

keywords = "Biopterine d-Glucoside, Protecting Group, Pteridine, Pterine Glycoside, Selective α-Glycosylation",

author = "Tadashi Hanaya and Hiroki Baba and Hiroshi Yamamoto",

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doi = "10.3987/COM-08-S(F)60",

language = "English",

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journal = "Heterocycles",

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publisher = "Japan Institute of Heterocyclic Chemistry",

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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

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First synthesis of biopterin α-D-glucoside

Abstract

Keywords

ASJC Scopus subject areas

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