Novel preparation of a 2′-O-acetyl-1′-O-(4-methoxybenzyl)-L- biopterin derivative, a versatile precursor for a selective synthesis of L-biopterin glycosides

Tadashi Hanaya; Hiroki Toyota; Hiroshi Yamamoto

doi:10.1055/s-2006-949620

Novel preparation of a 2′-O-acetyl-1′-O-(4-methoxybenzyl)-L- biopterin derivative, a versatile precursor for a selective synthesis of L-biopterin glycosides

Tadashi Hanaya, Hiroki Toyota, Hiroshi Yamamoto

Institute for Education and Student Services

Research output: Contribution to journal › Article

15 Citations (Scopus)

Abstract

L-Rhamnose was converted, over a 13-step-sequence, into 2′-O-acetyl-N²-(N,N-dimethylaminomethylene)-1′-O-(4- methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]-L-biopterin, an appropriately protected precursor of 1′-O- and 2′-O-monoglycosyl-L-biopterin. Thus, the first selective synthesis of these L-biopterin glycosides was accomplished by treatment of the precursor with either DDQ or sodium methoxide, then with tetra-O-benzoyl-α-D-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the remaining protecting groups.

Original language	English
Pages (from-to)	2075-2078
Number of pages	4
Journal	Synlett
Issue number	13
DOIs	https://doi.org/10.1055/s-2006-949620
Publication status	Published - Aug 17 2006

Fingerprint

Biopterin

Glycosides

Derivatives

Rhamnose

Bromides

Methanol

Keywords

Glycosylations
L-biopterin glycosides
Limipterin
Protecting groups
Pteridine

ASJC Scopus subject areas

Organic Chemistry

Cite this

Hanaya, T., Toyota, H., & Yamamoto, H. (2006). Novel preparation of a 2′-O-acetyl-1′-O-(4-methoxybenzyl)-L- biopterin derivative, a versatile precursor for a selective synthesis of L-biopterin glycosides. Synlett, (13), 2075-2078. https://doi.org/10.1055/s-2006-949620

Novel preparation of a 2′-O-acetyl-1′-O-(4-methoxybenzyl)-L- biopterin derivative, a versatile precursor for a selective synthesis of L-biopterin glycosides. / Hanaya, Tadashi; Toyota, Hiroki; Yamamoto, Hiroshi.

In: Synlett, No. 13, 17.08.2006, p. 2075-2078.

Research output: Contribution to journal › Article

Hanaya, T, Toyota, H & Yamamoto, H 2006, 'Novel preparation of a 2′-O-acetyl-1′-O-(4-methoxybenzyl)-L- biopterin derivative, a versatile precursor for a selective synthesis of L-biopterin glycosides', Synlett, no. 13, pp. 2075-2078. https://doi.org/10.1055/s-2006-949620

Hanaya T, Toyota H, Yamamoto H. Novel preparation of a 2′-O-acetyl-1′-O-(4-methoxybenzyl)-L- biopterin derivative, a versatile precursor for a selective synthesis of L-biopterin glycosides. Synlett. 2006 Aug 17;(13):2075-2078. https://doi.org/10.1055/s-2006-949620

Hanaya, Tadashi ; Toyota, Hiroki ; Yamamoto, Hiroshi. / Novel preparation of a 2′-O-acetyl-1′-O-(4-methoxybenzyl)-L- biopterin derivative, a versatile precursor for a selective synthesis of L-biopterin glycosides. In: Synlett. 2006 ; No. 13. pp. 2075-2078.

@article{7d3fafc10b7f4b468a389e961e33618d,

title = "Novel preparation of a 2′-O-acetyl-1′-O-(4-methoxybenzyl)-L- biopterin derivative, a versatile precursor for a selective synthesis of L-biopterin glycosides",

abstract = "L-Rhamnose was converted, over a 13-step-sequence, into 2′-O-acetyl-N2-(N,N-dimethylaminomethylene)-1′-O-(4- methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]-L-biopterin, an appropriately protected precursor of 1′-O- and 2′-O-monoglycosyl-L-biopterin. Thus, the first selective synthesis of these L-biopterin glycosides was accomplished by treatment of the precursor with either DDQ or sodium methoxide, then with tetra-O-benzoyl-α-D-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the remaining protecting groups.",

keywords = "Glycosylations, L-biopterin glycosides, Limipterin, Protecting groups, Pteridine",

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

year = "2006",

month = "8",

day = "17",

doi = "10.1055/s-2006-949620",

language = "English",

pages = "2075--2078",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "13",

}

TY - JOUR

T1 - Novel preparation of a 2′-O-acetyl-1′-O-(4-methoxybenzyl)-L- biopterin derivative, a versatile precursor for a selective synthesis of L-biopterin glycosides

AU - Hanaya, Tadashi

AU - Toyota, Hiroki

AU - Yamamoto, Hiroshi

PY - 2006/8/17

Y1 - 2006/8/17

N2 - L-Rhamnose was converted, over a 13-step-sequence, into 2′-O-acetyl-N2-(N,N-dimethylaminomethylene)-1′-O-(4- methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]-L-biopterin, an appropriately protected precursor of 1′-O- and 2′-O-monoglycosyl-L-biopterin. Thus, the first selective synthesis of these L-biopterin glycosides was accomplished by treatment of the precursor with either DDQ or sodium methoxide, then with tetra-O-benzoyl-α-D-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the remaining protecting groups.

AB - L-Rhamnose was converted, over a 13-step-sequence, into 2′-O-acetyl-N2-(N,N-dimethylaminomethylene)-1′-O-(4- methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]-L-biopterin, an appropriately protected precursor of 1′-O- and 2′-O-monoglycosyl-L-biopterin. Thus, the first selective synthesis of these L-biopterin glycosides was accomplished by treatment of the precursor with either DDQ or sodium methoxide, then with tetra-O-benzoyl-α-D-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the remaining protecting groups.

KW - Glycosylations

KW - L-biopterin glycosides

KW - Limipterin

KW - Protecting groups

KW - Pteridine

UR - http://www.scopus.com/inward/record.url?scp=33748286171&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33748286171&partnerID=8YFLogxK

U2 - 10.1055/s-2006-949620

DO - 10.1055/s-2006-949620

M3 - Article

AN - SCOPUS:33748286171

SP - 2075

EP - 2078

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 13

ER -

Access to Document

10.1055/s-2006-949620