First synthesis of a natural isoxanthopterin glycoside, asperopterin-A

Tadashi Hanaya; Kazumasa Ejiri; Hiroshi Yamamoto

doi:10.3987/COM-11-S(P)57

First synthesis of a natural isoxanthopterin glycoside, asperopterin-A

Tadashi Hanaya, Kazumasa Ejiri, Hiroshi Yamamoto

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5 Citations (Scopus)

Abstract

The key precursor, N ²-(N,N-dimethylaminomethylene)-6- hydroxymethyl- 8-methyl-3-[2-(4-nitrophenyl)ethyl]-7-xanthopterin (9) was efficiently prepared from 2,5-diamino-6-methylamino-3H-pyrimidin-4-one (3) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (11). The first synthesis of asperopterin-A (2b) was achieved by treatment of 9 with 1-O-acetyl-2,3,5- tri-O-benzoyl-β-D-ribofuranose (15) in the presence of tin(IV) chloride, followed by removal of the protecting groups.

Original language	English
Pages (from-to)	801-813
Number of pages	13
Journal	Heterocycles
Volume	84
Issue number	2
DOIs	https://doi.org/10.3987/COM-11-S(P)57
Publication status	Published - 2012

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "First synthesis of a natural isoxanthopterin glycoside, asperopterin-A",

abstract = "The key precursor, N 2-(N,N-dimethylaminomethylene)-6- hydroxymethyl- 8-methyl-3-[2-(4-nitrophenyl)ethyl]-7-xanthopterin (9) was efficiently prepared from 2,5-diamino-6-methylamino-3H-pyrimidin-4-one (3) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (11). The first synthesis of asperopterin-A (2b) was achieved by treatment of 9 with 1-O-acetyl-2,3,5- tri-O-benzoyl-β-D-ribofuranose (15) in the presence of tin(IV) chloride, followed by removal of the protecting groups.",

author = "Tadashi Hanaya and Kazumasa Ejiri and Hiroshi Yamamoto",

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doi = "10.3987/COM-11-S(P)57",

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T1 - First synthesis of a natural isoxanthopterin glycoside, asperopterin-A

AU - Hanaya, Tadashi

AU - Ejiri, Kazumasa

AU - Yamamoto, Hiroshi

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N2 - The key precursor, N 2-(N,N-dimethylaminomethylene)-6- hydroxymethyl- 8-methyl-3-[2-(4-nitrophenyl)ethyl]-7-xanthopterin (9) was efficiently prepared from 2,5-diamino-6-methylamino-3H-pyrimidin-4-one (3) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (11). The first synthesis of asperopterin-A (2b) was achieved by treatment of 9 with 1-O-acetyl-2,3,5- tri-O-benzoyl-β-D-ribofuranose (15) in the presence of tin(IV) chloride, followed by removal of the protecting groups.

AB - The key precursor, N 2-(N,N-dimethylaminomethylene)-6- hydroxymethyl- 8-methyl-3-[2-(4-nitrophenyl)ethyl]-7-xanthopterin (9) was efficiently prepared from 2,5-diamino-6-methylamino-3H-pyrimidin-4-one (3) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (11). The first synthesis of asperopterin-A (2b) was achieved by treatment of 9 with 1-O-acetyl-2,3,5- tri-O-benzoyl-β-D-ribofuranose (15) in the presence of tin(IV) chloride, followed by removal of the protecting groups.

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