Carbohydrate research

Expeditious synthesis of enantiopure symmetrical macroheterocycles by ring-closing metathesis of ether and tether-linked 1, 2-O-isopropylidenefuranosides

G Biswas, J Sengupta, M Nath, A Bhattacharjya

Index: Biswas, Goutam; Sengupta, Jhimli; Nath, Madhumita; Bhattacharjya, Anup Carbohydrate Research, 2005 , vol. 340, # 4 p. 567 - 578

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Citation Number: 5

Abstract

Bis-olefinic symmetrical carbohydrate derivatives were prepared by joining two 1, 2-O- isopropylidenefuranose units either through an ether linkage or by a tether of variable size. The ring-closing metathesis (RCM) of these substrates using Grubbs' first-generation catalyst led to the synthesis of enantiopure symmetrical macroheterocycles containing nine- to twenty-five-membered rings fused to the 1, 2-O-isopropylidenefuranose ring.