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JOURNAL ARTICLE
RESEARCH SUPPORT, NON-U.S. GOV'T
Regioselective 5-O-Opening of Conformationally Locked 3,5-O-Di-tert-butylsilylene-d-galactofuranosides. Synthesis of (1→5)-β-d-Galactofuranosyl Derivatives.
Journal of Organic Chemistry 2016 October 22
The use of thiogalactofuranoside as donors for the construction of internal Galf containing oligosaccharide is limited, probably due to the difficulty to functionalize thiogalactofuranoside derivatives showing O-2, O-3, and O-5 with similar reactivity. An efficient method for complete regioselective 5-O-opening of conformationally restricted 3,5-O-di-tert-butylsilylene-d-galactofuranoside derivatives was developed. The use of a solution nBu4 NF (1.1 equiv) in CH2 Cl2 on 6 gave the 5-OH free derivative 10 as the only product (90%). 3-O-Di-tert-butylhydroxysilyl derivative 10 was stable upon purification and glycosylation reaction. Preactivation of conformationally restricted thioglycoside 6 employing p-NO2 -benzensulfenyl chloride/AgOTf followed by condensation over the 5-OH thioglycoside acceptor 10 gave the corresponding disaccharide 12 without autocondensation byproduct. Regioselective 5-O-deprotection was also successfully performed over the (1→5)-β-d-galactofuranosyl di- and trisaccharide derivatives 12 and 13. This methodology allowed the differentiation between the secondary hydroxyl groups OH-3 and OH-5 of 1,2-cis or 1,2-trans d-galactofuranoside derivatives, and it still constitutes an innovative approach to access oligosaccharides of pharmacological importance.
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