An efficient synthesis of 2′-O-(β-d-glucopyranosyl)- and 2′-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-biopterins

Tadashi Hanaya, Kazuyuki Soranaka, Koichiro Harada, Hiroshi Yamaguchi, Ryo Suzuki, Yusumi Endo, Hiroshi Yamamoto, Wolfgang Pfleiderer

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

N2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1′,2′-di-O-trimethylsilyl-L-biopterin (6) was prepared from L-biopterin in 5 steps. Glycosylation of 6 with 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate (9) and 1,3,4,6-tetra-O-acetyl-2-phtalimido-β-D-glucopyranose (10) respectively afforded the corresponding 2′-O-(β-D-glucopyranosyl) derivatives (12b, 12c) as major products. Removal of protecting groups of 12c provided naturally occurring limipterin (2).

Original languageEnglish
Pages (from-to)299-310
Number of pages12
JournalHeterocycles
Volume67
Issue number1
DOIs
Publication statusPublished - Jan 1 2006

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Biopterin
Glycosylation
Derivatives

ASJC Scopus subject areas

  • Organic Chemistry

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An efficient synthesis of 2′-O-(β-d-glucopyranosyl)- and 2′-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-biopterins. / Hanaya, Tadashi; Soranaka, Kazuyuki; Harada, Koichiro; Yamaguchi, Hiroshi; Suzuki, Ryo; Endo, Yusumi; Yamamoto, Hiroshi; Pfleiderer, Wolfgang.

In: Heterocycles, Vol. 67, No. 1, 01.01.2006, p. 299-310.

Research output: Contribution to journalArticle

Hanaya, T, Soranaka, K, Harada, K, Yamaguchi, H, Suzuki, R, Endo, Y, Yamamoto, H & Pfleiderer, W 2006, 'An efficient synthesis of 2′-O-(β-d-glucopyranosyl)- and 2′-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-biopterins', Heterocycles, vol. 67, no. 1, pp. 299-310. https://doi.org/10.3987/COM-05-S(T)28
Hanaya, Tadashi ; Soranaka, Kazuyuki ; Harada, Koichiro ; Yamaguchi, Hiroshi ; Suzuki, Ryo ; Endo, Yusumi ; Yamamoto, Hiroshi ; Pfleiderer, Wolfgang. / An efficient synthesis of 2′-O-(β-d-glucopyranosyl)- and 2′-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-biopterins. In: Heterocycles. 2006 ; Vol. 67, No. 1. pp. 299-310.
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abstract = "N2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1′,2′-di-O-trimethylsilyl-L-biopterin (6) was prepared from L-biopterin in 5 steps. Glycosylation of 6 with 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate (9) and 1,3,4,6-tetra-O-acetyl-2-phtalimido-β-D-glucopyranose (10) respectively afforded the corresponding 2′-O-(β-D-glucopyranosyl) derivatives (12b, 12c) as major products. Removal of protecting groups of 12c provided naturally occurring limipterin (2).",
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AU - Soranaka, Kazuyuki

AU - Harada, Koichiro

AU - Yamaguchi, Hiroshi

AU - Suzuki, Ryo

AU - Endo, Yusumi

AU - Yamamoto, Hiroshi

AU - Pfleiderer, Wolfgang

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AB - N2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1′,2′-di-O-trimethylsilyl-L-biopterin (6) was prepared from L-biopterin in 5 steps. Glycosylation of 6 with 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate (9) and 1,3,4,6-tetra-O-acetyl-2-phtalimido-β-D-glucopyranose (10) respectively afforded the corresponding 2′-O-(β-D-glucopyranosyl) derivatives (12b, 12c) as major products. Removal of protecting groups of 12c provided naturally occurring limipterin (2).

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