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

研究成果 › 査読

3 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	747-753
ページ数	7
ジャーナル	Heterocycles
巻	77
号	2
DOI	https://doi.org/10.3987/COM-08-S(F)60
出版ステータス	Published - 2月 1 2009

ASJC Scopus subject areas

分析化学
薬理学
有機化学

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10.3987/COM-08-S(F)60

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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",

year = "2009",

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

language = "English",

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journal = "Heterocycles",

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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

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DO - 10.3987/COM-08-S(F)60

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JO - Heterocycles

JF - Heterocycles

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First synthesis of biopterin α-D-glucoside

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