67831-41-8Relevant academic research and scientific papers
Oxidative esterification of primary alcohols with TEMPO/CaCl2/Oxone under hydrous conditions
Hackbusch, Sven,Franz, Andreas H.
supporting information, p. 2873 - 2876 (2016/06/14)
Symmetric esters are important compounds in the chemical industry, which creates demand for simple and efficient synthetic routes. Oxidative esterification is a promising method to achieve these aims. Here, we show that TEMPO/CaCl2/Oxone forms a convenient catalytic system for the synthesis of the aforementioned symmetric esters from primary alcohols in a biphasic dichloromethane-water solvent mixture. The substrate scope of the reaction method is complementary to those previously published and the terminal oxidant appears to play an important role. In addition, the method is shown to oxidize thiols preferentially over alcohol functional groups to give disulfide-bridged compounds.
Regioselective removal of the anomeric O-benzyl from differentially protected carbohydrates
Jalsa, Nigel Kevin
supporting information; scheme or table, p. 6587 - 6590 (2012/02/03)
A mild, regioselective deprotection of the anomeric O-benzyl from multi-functionally protected carbohydrates via catalytic transfer hydrogenation is described. The protocol is tolerant of O-benzyl and O-benzylidene protections at non-anomeric positions, g
In situ activating glycosylation of 6-deoxysugars: Synthesis of O- α-D- fucosyl(1→4)-O-α-D-fucosyl-(1→4)-O-α-D-quinovosyl-(1→4)-D-quinovose
Koto, Shinkiti,Kusunoki, Ami,Hirooka, Motoko
, p. 967 - 976 (2007/10/03)
The linear tetrasaccharide, α-D-fucopyranosyl-(1→4)-a-D-fucopyranosyl- (1→4)-α-D-quinovopyranosyl-(1→4)-D-quinovopyranose, the sugar cluster of asterosaponin A from the starfish, Asterias amurensis, was synthesized in a convergent manner. We employed an i
Regio- and stereoselective synthesis of β-D-gluco-, α-L-ido-, and α- L-altropyranosiduronic acids from Δa4-uronates
Bazin, Helene G.,Wolff, Michael W.,Linhardt, Robert J.
, p. 144 - 152 (2007/10/03)
The stereoselective synthesis of β-D-glucopyranosiduronic, α-L- idopyranosiduronic, and α-L-altropyranosiduronic acids has been performed from different Δ4-uronate monosaccharides. Bromination of the C-4,5 double bond provided the trans-diaxial bromohydrin derivatives, which were converted to the corresponding epoxides in high yields. Direct reduction of the epoxides using boranetetrahydrofuran complex led to the corresponding glucuronic acids in low to good yields. Glucuronic acids were also obtained in satisfactory yields through a two-steps procedure involving bromination of the epoxide with titanium(IV) bromide followed by reduction using tributyltin hydride. Lewis acid-catalyzed rearrangement of these epoxides led to the corresponding α-L C-4 ketopyranosides adopting the 1C4 chair conformation. Hydride reduction afforded the α-L-idopyranosiduronic or the α-L- altropyranosiduronic acids, the stereoselectivity of the reduction being controlled by the appropriate substitution pattern.
Synthesis of monosaccharide-fused azetidines
Michaud, Thierry,Chanet-Ray, Josette,Chou, Sithan,Gelas, Jacques
, p. 253 - 269 (2007/10/03)
Primary amines reacted upon 4,6-ditosylates of glucopyranosides to give an azetidine ring fused on C-4 and C-6 of the pyranose ring. On the other hand, the 4,6-ditosylate of benzyl mannopyranoside led to the 4,6-diamino-4,6-dideoxy derivative in a good yield. All the compounds and their precursors were identified by 1H and 13C NMR spectroscopy. Assignments of proton signals were made unambiguously using homodecoupling experiments.
TOTAL SYNTHESIS OF THE MOLLU-SERIES GLYCOSYL CERAMIDES α-D-Manp-(1->3)-β-D-Manp-(1->4)-β-D-Glcp-(1->1)-Cer AND α-D-Manp-(1->3)-2)>-β-D-Manp-(1->4)-β-D-Glcp-(1->1)-Cer
Mori, Masato,Ito, Yukishige,Ogawa, Tomoya
, p. 199 - 224 (2007/10/02)
The mollu-series glycosphingolipids, O-α-D-mannopyranosyl-(1->3)-O-β-D-mannopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->1)-2-N-tetracosanoyl-(4E)-sphingenine and O-α-D-mannopyranosyl-(1->3)-O-2)>-O-β-D-mannopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->1)-2-N-tetracosanoyl-(4E)-sphingenine, were synthesized for the first time by using 2,3,4-tri-O-acetyl-D-xylopyranosyl trichloroacetimidate, methyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside, benzyl O-(4,6-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 9, and (2S,3R,4E)-2-azido-3-O-(tert-butyldiphenylsilyl)-4-octadecene-1,3-diol 6 as the key intermediates.The hexa-O-benzyl disaccharide 9 was prepared by coupling two monosaccharide synthons, namely, 2,3-di-O-allyl-4,6-di-O-benzyl-α-D-mannopyranosyl bromide and benzyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside.It was demonstrated that azide 6 was highly efficient as a synthon for the ceramide part in the coupling with both glycotriaosyl and glycotetraosyl donors, particularly in the presence of trimethylsilyl triflate.
