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

Cetin F. , Yenil N., Yuceer L.

CARBOHYDRATE RESEARCH, cilt.340, ss.2583-2589, 2005 (SCI İndekslerine Giren Dergi) identifier identifier identifier

  • Cilt numarası: 340 Konu: 17
  • Basım Tarihi: 2005
  • Doi Numarası: 10.1016/j.carres.2005.09.006
  • Sayfa Sayıları: ss.2583-2589


Sunlight-mediated photooxygenation of 3-O-acetyl and 3-O-methyl derivatives of 1,2-O-alkylidene-5(E)-eno-5,6,8-tride-oxy-alpha-D-xylo-oct-1,4-furano-7-uloses (1 a-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. (c) 2005 Elsevier Ltd. All rights reserved.