143899-79-0Relevant academic research and scientific papers
Studies related to carba-pyranoses: A radical decarboxylation approach to monocarba-disaccharides
Larsen, David S.,Lins, Roger J.,Stoodley, Richard J.,Trotter, Nicholas S.
, p. 1934 - 1942 (2007/10/03)
(1→1), (1→3) and (1→4) acetal-linked monocarba-disaccharides have been synthesised from a series of glucosylated γ- and δ-lactonic acids prepared from common intermediate 2, obtained from the Diels-Alder reaction of maleic anhydride and (E)-1-(2′,3′,4′, 6′-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-(trimethylsiloxy)buta-1, 3-diene 1. Thiohydroxamic ester 14, prepared from γ-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-β-D-glucopyranosyl)-2,4-dideoxy-5a-carba- β-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 acetylation gave the monocarbadisaccharides 1, 4, 6-tri-O-acetyl-3-O-(2′,3′,4′, 6′-tetra-O-acetyl-β-D-glucopyranosyl)-2-deoxy-5acarba-β-L- arabino-hexopyranose 21 and 1,2,4,6-tetra-O-acetyl-3-O-(2′,3′, 4′,6′-tetra-O-acetyl-β-D-glucopyranosyl)5a-carba-β-L- glucopyranose 23 respectively.
