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, vol.340, no.17, pp.2583-2589, 2005 (SCI-Expanded, Scopus) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 340 Issue: 17
  • Publication Date: 2005
  • Doi Number: 10.1016/j.carres.2005.09.006
  • Journal Name: Carbohydrate Research
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2583-2589
  • Keywords: endoperoxides, spiroketals, furano sugars, antimalarial drugs, antibiotics
  • Manisa Celal Bayar University Affiliated: Yes

Abstract

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.