25018-28-4Relevant academic research and scientific papers
Molecular sieves promote stereocontrolled αα-disaccharide formation via direct dimerization of free sugars
Posner, Gary H.,Bull, D. Scott
, p. 6279 - 6282 (1996)
Some commercial molecular sieves promote direct dimerization of free pyranose and furanose sugars stereoselectively into the corresponding α,α-disaccharides.
2-Allylphenyl glycosides as glycosyl donors for sugar coupling
Luo, Shun-Yuan,Tripathi, Ashish,Zulueta, Medel Manuel L.,Hung, Shang-Cheng
, p. 197 - 201 (2012/06/30)
Glycosylations employing 2-allylphenyl glycoside, a new type of stable glycosyl donor, were optimized and explored with a variety of acceptors promoted by ICl/AgOTf. The utility of the protocol was further demonstrated with an efficient synthesis of the disaccharide fragment of bleomycins.
Formation of O-glycosidic linkages from 1-hydroxy sugars by bismuth(III) triflate-catalyzed dehydrative glycosidation
Yamanoi, Takashi,Inoue, Ryo,Matsuda, Sho,Iwao, Kazuya,Oda, Yoshiki,Yoshida, Akihiro,Hamasaki, Keita
experimental part, p. 445 - 460 (2009/09/30)
This paper describes the direct formation of various O-glycosidic linkages from 1-hydroxy sugars by bismuth(III) triflate-catalyzed dehydrative glycosidation. The condensation reactions of 1 -hydroxy sugars with some primary alcohols in the presence of on
2-Allyloxyphenyl glycoside as a new and stable type of glycosyl donors
Lee, Jinq-Chyi,Pan, Guan-Rong,Kulkarni, Suvarn S.,Luo, Shun-Yuan,Liao, Chun-Chen,Hung, Shang-Cheng
, p. 1621 - 1624 (2007/10/03)
A high-yielding coupling of a new and stable type of glycosyl donors, namely 2-allyloxyphenyl glycoside, with a variety of alcohols via NIS/TfOH reagent combination as effective activators at room temperature is described here.
Sulfoxide Covalent Catalysis: Application to Glycosidic Bond Formation
Boebel, Timothy A.,Gin, David Y.
, p. 5874 - 5877 (2007/10/03)
A versatile glycosylation reaction is used to establish the process of sulfoxide covalent catalysis. Hemiacetals are activated by benzenesulfonic anhydride and a dialkyl sulfoxide catalyst, nBu2SO, for coupling with various nucleophiles (Nu; se
Synthesis of methyl O-α-D-mannosyl-(1→4)-[(3-O-methyl-α-D-mannosyl) -(1→4)-]n3-O-methyl-α-D-mannosides (n = 0, 1, and 2) via dehydrative glycosylation
Hirooka, Motoko,Terayama, Megumi,Mitani, Emi,Koto, Shinkiti,Miura, Asako,Chiba, Kayo,Takabatake, Ayano,Tashiro, Takako
, p. 1301 - 1309 (2007/10/03)
Methyl O-α-D-mannopyranosyl-(1→4)-[(3-O-methyl-α-D-mannopyranosyl -(1→4)-]n3-O-methyl-α-D-mannopyra-nosides (n = 0, 1, and 2), the lowest homologs related to the 3-O-methylmannose polysaccharides (MMP) from Mycobacterium smegmatis, were synthesized via dehydrative glycosylation reactions. The reagent systems, composed of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and 1, 8-diazabicyclo[5.4.0]undec-7-ene, and of trimethylsilyl trifuloromethanesulfonate and pyridine were useful.
Rational design and synthesis of a 1,1-linked disaccharide that is 5 times as active as sialyl Lewis X in binding to E-selectin
Hiruma, Kazumi,Kajimoto, Tetsuya,Weitz-Schmidt, Gabriel,Ollmann, Ian,Wong, Chi-Huey
, p. 9265 - 9270 (2007/10/03)
We describe here a rational design and synthesis of (3-O-carboxymethyl)-β-D-galactopyranosyl α-D-mannopyranoside which is 5 times as active as sialyl Lewis X in binding to E-selectin and also effective against P- and L-selectin. A new method for the 1,1-g
TMS triflate induced synthesis of 1,1'-disaccharides from 1-hydroxy sugars
Nishizawa,Garcia,Noguchi,Komatsu,Hatakeyama,Yamada
, p. 2400 - 2402 (2007/10/02)
A variety of 1,1'-disaccharides have been prepared by TMS triflate induced coupling of 1-hydroxy sugars in reasonable yield.
Synthesis and glycosylation shift of 1,1'-disaccharides
Nishizawa,Kodama,Yamane,Kayano,Hatakeyama,Yamada
, p. 982 - 984 (2007/10/02)
Nineteen kinds of nonreducing 1,1'-disaccharides have synthesized by modified Koenigs-Knorr method, and characterized by NMR. The glycosylation shift of each anomeric carbon has been estimated.
The Use of O-Glycosyl Trichloroacetimidates in The Synthesis of Unsymmetrical Trehalose Analogues
Ronnow, Tor E. C. L.,Meldal, Morten,Bock, Klaus
, p. 2109 - 2122 (2007/10/02)
The coupling of O-glycosyl trichloroacetimidates with 2,3,4,6-tetra-O-benzylated monosaccharides (gluco, manno, galacto) promoted by TMSOTf is described, and the compositions of the crude reaction mixtures, determined by 13C NMR spectroscopy, are presente
