110415-60-6Relevant academic research and scientific papers
Conversion of pyranose glycals to furanose derivatives: A new route to oligofuranosides
D'Souza, Francis W.,Cheshev, Pavel E.,Ayers, Joseph D.,Lowary, Todd L.
, p. 9037 - 9044 (1998)
Acetylated pyranose glycals have been converted through a convenient three-step process into protected furanose reducing sugars. Ozonolysis of 2,3,5-tri-O-acetyl-glucal or 2,3,5-tri-O-acetylgalactal, followed by treatment with dimethyl sulfide and then hydrolysis gave respectively protected arabinofuranose (6) and lyxofuranose (7) derivatives. Conversion of these hemiacetals to oligosaccharides was explored using a number of methods. Activation of 6 or 7 in situ afforded glycosides in modest yield and stereoselectivity. Glycosylation of tetraacetates 16 and 18, obtained from 6 and 7, gave similar results. However, thioglycosides 17 and 19, also derived from 6 and 7, were found to be effective glycosyl donors, producing products in good to excellent yields and with high stereoselectivities. The method was also used to synthesize a disaccharide in which one residue contained uniform 13C enrichment.
Organoboron Monosaccharides, XVI. Selective Syntheses of the Methyl α-D-Furanosides of Lyxose and Mannose Using Ethyl(dimethoxy)borane
Dahlhoff, Wilhelm V.,Fenzl, Wolfgang,Koester, Roland
, p. 807 - 810 (2007/10/02)
Ethyl(dimethoxy)borane is prepared by a two-step method involving reaction of triethylboroxin with 1,4-butanediol in a molar ratio of 1:3 to give oligomeric 1,4-butanediyldioxyethylboranes which are then treated with methanol.D-Lyxose (1) reacts selectively with ethyl(dimethoxy)borane in the presence of acidic ion exchange resin to form methyl 2,3-O-ethylboranediyl-α-D-lyxofuranoside (2) which is deboronated to give methyl α-D-lyxofuranoside (4).Similarly, D-mannose (6) reacts to give methyl 2,3:5,6-bis-O-ethylboranediyl-α-d-mannofuranoside (7), the deprotection of which yields methyl α-D-mannofuranoside (8).
