Studies of Nucleosides and Nucleotides. XLII. Purine Cyclonucleosides. (9). Synthesis of Adenine Cyclonucleosides having 8, 2'-and 8, 3'-O-Anhydro Linkages

• 池原 森男

• 金岡 祐一

抄録

2'-O-Triisopropylbenzenesulfonyl-8-bromoadenosine was converted to 8-oxy derivative either by treatment with sodium acetate in acetic acid or by sodium acetate in acetic anhydride-acetic acid mixture. 2'-Triisopropylbenzenesulfonyl-8-oxy-adenosine or its N⁶, 3', 5'-triacetyl derivative was cyclized to 8, 2'-anhydro-8-oxy-9-β-D-arabinofuranosyladenine with sodium acetate in dimethyl formamide (DMF). Cyclization of 2'- and 3'-triisopropylbenzenesulfonyl-8-oxy derivative was kinetically followed and it was found that the former cyclized easier than the latter compound and decomposition of both cyclonucleosides differed greatly in its rate. Using short cyclization time 8, 3'-anhydro-8-oxy-9-β-D-xylofuranosyladenine was first synthesized from 3'-O-triisopropylbenzenesulfonyl-8-oxyadenosine. Optical rotatory dispersion (ORD) and circular dichroism (CD) curves of these cyclonucleosides were described.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 18 (12), 2401-2406, 1970

  公益社団法人 日本薬学会

キーワード

• Drug Discovery
• General Chemistry
• General Medicine

詳細情報

• CRID: 1390001204168440320
• NII論文ID: 110003632243
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.18.2401
• COI: 1:CAS:528:DyaE3MXmsVelsA%3D%3D
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/18/12/18_12_2401/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1971087505
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可