First synthesis of tepidopterin [2′-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-threo-biopterin]

Tadashi Hanaya; Hiroki Baba; Hiroshi Yamamoto

doi:10.1016/j.carres.2007.06.017

First synthesis of tepidopterin [2′-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-threo-biopterin]

Tadashi Hanaya, Hiroki Baba, Hiroshi Yamamoto

研究成果 › 査読

9 被引用数 (Scopus)

抄録

N²-(N,N-Dimethylaminomethylene)-1′-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]-l-threo-biopterin (14) was prepared from l-xylose in an 11-step-sequence. The first synthesis of tepidopterin (3) was achieved by treatment of 14 with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl bromide 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）	2159-2162
ページ数	4
ジャーナル	Carbohydrate Research
巻	342
号	15
DOI	https://doi.org/10.1016/j.carres.2007.06.017
出版ステータス	Published - 11月 5 2007

ASJC Scopus subject areas

分析化学
生化学
有機化学

文献へのアクセス

10.1016/j.carres.2007.06.017

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引用スタイル

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title = "First synthesis of tepidopterin [2′-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-threo-biopterin]",

abstract = "N2-(N,N-Dimethylaminomethylene)-1′-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]-l-threo-biopterin (14) was prepared from l-xylose in an 11-step-sequence. The first synthesis of tepidopterin (3) was achieved by treatment of 14 with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups.",

keywords = "Glycosylation, Pteridine, Pterin glycoside, Tepidopterin, l-threo-Biopterin",

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

year = "2007",

month = nov,

day = "5",

doi = "10.1016/j.carres.2007.06.017",

language = "English",

volume = "342",

pages = "2159--2162",

journal = "Carbohydrate Research",

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TY - JOUR

T1 - First synthesis of tepidopterin [2′-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-threo-biopterin]

AU - Hanaya, Tadashi

AU - Baba, Hiroki

AU - Yamamoto, Hiroshi

PY - 2007/11/5

Y1 - 2007/11/5

N2 - N2-(N,N-Dimethylaminomethylene)-1′-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]-l-threo-biopterin (14) was prepared from l-xylose in an 11-step-sequence. The first synthesis of tepidopterin (3) was achieved by treatment of 14 with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups.

AB - N2-(N,N-Dimethylaminomethylene)-1′-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]-l-threo-biopterin (14) was prepared from l-xylose in an 11-step-sequence. The first synthesis of tepidopterin (3) was achieved by treatment of 14 with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups.

KW - Glycosylation

KW - Pteridine

KW - Pterin glycoside

KW - Tepidopterin

KW - l-threo-Biopterin

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DO - 10.1016/j.carres.2007.06.017

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JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 15

ER -

First synthesis of tepidopterin [2′-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-threo-biopterin]

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