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

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

9 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2159-2162
Number of pages	4
Journal	Carbohydrate Research
Volume	342
Issue number	15
DOIs	https://doi.org/10.1016/j.carres.2007.06.017
Publication status	Published - Nov 5 2007

Keywords

Glycosylation
Pteridine
Pterin glycoside
Tepidopterin
l-threo-Biopterin

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

Access to Document

10.1016/j.carres.2007.06.017

Cite this

@article{043b96c15c75409c9d603dd5c0f1bc69,

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",

issn = "0008-6215",

publisher = "Elsevier BV",

number = "15",

}

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

UR - http://www.scopus.com/inward/record.url?scp=34548155653&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34548155653&partnerID=8YFLogxK

U2 - 10.1016/j.carres.2007.06.017

DO - 10.1016/j.carres.2007.06.017

M3 - Article

C2 - 17631283

AN - SCOPUS:34548155653

SN - 0008-6215

VL - 342

SP - 2159

EP - 2162

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]

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this