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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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

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ASJC Scopus subject areas

Analytical Chemistry
Organic Chemistry
Pharmacology

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Hanaya, T., Ejiri, K., & Yamamoto, H. (2012). First synthesis of a natural isoxanthopterin glycoside, asperopterin-A. Heterocycles, 84(2), 801-813. https://doi.org/10.3987/COM-11-S(P)57

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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.",

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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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10.3987/COM-11-S(P)57