25018-28-4Relevant articles and documents
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.
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
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.