MISC

2017年1月

EFFICIENT TOTAL SYNTHESES OF NATURAL NEOPTERIN GLYCOSIDES: NEOPTERIN GLUCRONIDE AND SOLFAPTERIN

HETEROCYCLES
  • Tadashi Hanaya
  • ,
  • Katsuya Iwasaki
  • ,
  • Kaori Saeki
  • ,
  • Takafumi Hattori

95
1
開始ページ
390
終了ページ
409
記述言語
英語
掲載種別
DOI
10.3987/COM-16-S(S)32
出版者・発行元
PERGAMON-ELSEVIER SCIENCE LTD

1',2'-Di-O-acetyl-N-2-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]neopterin (11a) and its 1',2'-di-O-benzoyl analog (11b) were prepared from neopterin in 5 steps, respectively. Glycosylation of 11a with methyl 2,3,4-tri-O-benzoyl-alpha-D-glucopyranosyluronate bromide (15b) in the presence of silver triflate afforded the corresponding 3'-O-(beta-D-glucopyranosyl)neopterin derivative (18) in 64% yield. The similar treatment of 11b with 2-azido-3,4,6-tri-O-benzoyl-2-deoxy-alpha-D-glucopyranosyl bromide (21b) provided the corresponding 3'-O-(alpha-D-glucopyranosyl)neopterin derivative (23a) in 58% yield. The first syntheses of neopterin glucronide (5) and solfapterin (6) were achieved by successive removal of the protecting groups of 18 and 23a, respectively.


リンク情報
DOI
https://doi.org/10.3987/COM-16-S(S)32
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000405885400032&DestApp=WOS_CPL

エクスポート
BibTeX RIS