First synthesis of asperopterin A, an isoxanthopterin glycoside from Aspergillus oryzae

Pteridines

Hanaya Tadashi¹  Yamamoto Hiroshi² 

[1] Faculty of Science, Department of Chemistry, Okayama University, Tsushima-naka, Kita-ku, Okayama 700–8530, Japan;School of Pharmacy, Shujitsu University, Nishigawara, Naka-ku, Okayama, Japan;

关键词: asperopterin;    glycosylation;    isoxanthopterin;    protecting groups;    pterin glycoside;   

DOI  :  10.1515/pterid-2013-0005

来源: DOAJ

【 摘 要 】

The key precursor, N2-(N,N-dimethylaminomethylene)-6-hydroxymethyl-8-methyl-3-[2-(4-nitrophenyl)ethyl]-7-xanthopterin (16) was efficiently prepared from 2,5-diamino-6-methylamino-3H-pyrimidin-4-one (5) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (12), followed by the protection of the pteridine ring. Glycosylation of 16 with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (18) in the presence of tin(IV) chloride yielded the corresponding β-D-ribofuranoside. Successive removal of the protecting groups of the resulting D-ribofuranoside provided asperopterin A (4b).

【 授权许可】

Unknown