Stable spiro-endoperoxides by sunlight-mediated photooxygenation of 1,2-O-alkylidene-5(E)-eno-5,6,8-trideoxy-α-D-xylo-oct-1,4-furano-7-uloses

Çetin F., YENİL N., Yüceer L.

Carbohydrate Research, cilt.340, sa.17, ss.2583-2589, 2005 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 340 Sayı: 17
  • Basım Tarihi: 2005
  • Doi Numarası: 10.1016/j.carres.2005.09.006
  • Dergi Adı: Carbohydrate Research
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2583-2589
  • Anahtar Kelimeler: endoperoxides, spiroketals, furano sugars, antimalarial drugs, antibiotics
  • Manisa Celal Bayar Üniversitesi Adresli: Evet

Özet

Sunlight-mediated photooxygenation of 3-O-acetyl and 3-O-methyl derivatives of 1,2-O-alkylidene-5(E)-eno-5,6,8-trideoxy-α-D-xylo-oct-1,4-furano-7- uloses (1a-e) in carbon tetrachloride solution gave stable 4,7-epidioxy derivatives in 4R (2a-e) and 4S (3a-e) configurations. The presence of an endo alkyl, on the 1,2-O-alkylidene group and its size, resulted in an increase of the yield of the 4S isomers. 3-O-Acetyl derivatives yielded products as a mixture of C-7 anomers, whereas 3-O-methyl derivatives gave pure single stereoisomers. © 2005 Elsevier Ltd. All rights reserved.