Studies related to carba-pyranoses: a radical decarboxylation approach to monocarba-disaccharides

Organic & Biomolecular Chemistry
David S LarsenNicholas S Trotter

Abstract

(1--> 1), (1--> 3) and (1--> 4) acetal-linked monocarba-disaccharides have been synthesised from a series of glucosylated gamma- and delta-lactonic acids prepared from common intermediate, obtained from the Diels-Alder reaction of maleic anhydride and (E)-1-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-(trimethylsiloxy)buta-1,3-diene 1. Thiohydroxamic ester 14, prepared from gamma-lactonic acid 9, gave, upon treatment with tert-butyl thiol and light, the lactone 15. Subsequent lithium aluminium hydride reduction and acetylation gave the (1--> 3) acetal-linked monocarbadisaccharides 1,6-di-O-acetyl-3-O-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyl)-2,4-dideoxy-5a-carba-beta-L-threo-hexopyranose 16. In a similar manner, protected monocarba-disaccharides 13, 19, 30, and 35 possessing L-ido, L-xylo, D-arabino and L-ido configurations of the carba-pyranose ring have been prepared. Treatment of thiohydroxamic esters 14 and 17 with either tert-butyl thiol or trityl thiol, dimethyl sulfide, oxygen and light gave alcohols 20 and 22. Subsequent lithium aluminium hydride reduction and aceytlation gave the monocarbadisaccharides 1,4,6-tri-O-acetyl-3-O-[2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyl]-2-deoxy-5a-carba-beta-L-...Continue Reading

Citations

Feb 15, 2000·Bioorganic & Medicinal Chemistry Letters·N KashiharaS Nishiyama
Jul 31, 2018·Chemistry, an Asian Journal·Phillip S GrantDaniel P Furkert
Nov 22, 2018·Angewandte Chemie·Padon ChuentragoolVladimir Gevorgyan
Sep 2, 2004·Chemical & Pharmaceutical Bulletin·Junichi KamataHiroyuki Sugumi
May 11, 2019·Chemistry : a European Journal·Basudev SahooRuben Martin

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