The Wittig-cyclization procedure: acid promoted intramolecular formation of 3-C-branched-chain 3,6-anhydro furano sugars via 2′-oxopropylene derivatives

Ay K., Çetin F., Yüceer L.

Carbohydrate Research, cilt.342, sa.8, ss.1091-1095, 2007 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 342 Sayı: 8
  • Basım Tarihi: 2007
  • Doi Numarası: 10.1016/j.carres.2007.02.021
  • Dergi Adı: Carbohydrate Research
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1091-1095
  • Anahtar Kelimeler: branched-chain sugars, anhydrosugars, Wittig-cyclization, intramolecular ring-closure
  • Manisa Celal Bayar Üniversitesi Adresli: Hayır

Özet

Some olefinic Wittig products, 3-deoxy-5,6-O-isopropylidene-3-C-(2′-oxopropylene)-1,2-O-alkylidene hexofuranose derivatives were converted to the branched-chain 3,6-anhydro-3-C-(2′-oxopropyl) derivatives on treatment with ion exchange resin Amberlite 120 (H+) in methanol-water at room temperature. Hydrolysis of 5,6-isopropylidene groups and intramolecular ring-closures took place in one pot reactions. © 2007 Elsevier Ltd. All rights reserved.