Tricyclic furanoid dichloroacetyl orthoesters of D-mannose from 1,2-O-trichloroethylidene-beta-D-mannofuranose


SALMAN Y., Kok G. , YUCEER L.

CARBOHYDRATE RESEARCH, cilt.339, ss.1739-1745, 2004 (SCI İndekslerine Giren Dergi) identifier identifier identifier

  • Cilt numarası: 339 Konu: 10
  • Basım Tarihi: 2004
  • Doi Numarası: 10.1016/j.carres.2004.05.012
  • Dergi Adı: CARBOHYDRATE RESEARCH
  • Sayfa Sayıları: ss.1739-1745

Özet

1,2- O-(R)-Trichloroethylidene-beta-D-mannofuranose (1) was obtained from the reaction Of D-mannose with chloral. Reaction of I with potassium tert-butoxide (3 M equiv) gave the thermodynamically stable 1,2,5-0-orthodichloroacetyl-beta-D-mannofuranose as the sole product whereas 1.5 M equiv of reagent gave the kinetically controlled 1,2,3- O-orthodichloroacetyl-beta-D -mannofuranose (10) as the main product. Orthoester 10 gave the 5,6-isopropylidene derivative, which was also obtained from the reaction of 5,6-O-isopropylidene-1,2-O-(R)-trichloroethylidene-beta-D-mannofuranose with potassium tert-butoxide (1.5 M equiv). These novel orthoesters are expected to prove useful as protecting groups and as building blocks in the formations of new mannofuranisidic units. (C) 2004 Elsevier Ltd. All rights reserved.