First Synthesis of a Natural Isoxanthopterin Glycoside, Asperopterin-A | Zendy

Tadashi Hanaya | Zendy; Kazumasa Ejiri | Zendy; Hiroshi Yamamoto | Zendy

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First Synthesis of a Natural Isoxanthopterin Glycoside, Asperopterin-A

Author(s) -

Tadashi Hanaya,

Kazumasa Ejiri,

Hiroshi Yamamoto

Publication year - 2011

Publication title -

heterocycles

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.242

H-Index - 64

eISSN - 1881-0942

pISSN - 0385-5414

DOI - 10.3987/com-11-s(p)57

Subject(s) - chemistry , glycoside , tin , hydroxymethyl , chloride , stereochemistry , organic chemistry

The key precursor, N-2-(N,N-dimethylaminomethylene)-6-hydroxymethy1-8-methyl-3[2-(4-nitrophenypethyl]-7-xanthopterin (9) was efficiently prepared from 2,5-diamino-6-methylam1no-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-benzoy1-beta-D-ribofuranose (15) in the presence of tin(IV) chloride, followed by removal of the protecting groups

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