117841-66-4

Upstream product

• 38768-84-2 Dibenzyl(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)phosphat 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 90357-89-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 
• 82300-58-1 dibezylphosphoryl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 942907-29-1 Imidazole-1-carboxylic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 74666-83-4 1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 79386-43-9 diphenyl 2,3,4,6-tetra-O-benzyl-α-D-glucosyl phosphate 
• 56822-49-2 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 339276-14-1 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 
• 920749-29-7 Pent-4-enoic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 810670-73-6 benzoxazol-2-yl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 142266-54-4 1,3-thiazolin-2-yl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 

Relevant academic research and scientific papers

[R4N] [AOT]: A surfactant ionic liquid as a mild glycosylation promoter

[RN4][AOT] is a versatile surfactant ionic liquid that can be used in combination with N-Iodosuccinimide to promote the room temperature glycosylation of thiophenyl glycoside donors. The conditions are mild, with no requirement for molecular si

Protecting group and solvent effects in electrochemical glycosylation

An investigation is undertaken into the roles of protecting groups and the solvent in the electrochemical-mediated glycosylation of manno thioglycosides. Herein notable differences are observed between electrochemical and chemical glycosylation. Georg Thi

Fluoropyridyl Sugars - Masked Imidate Glycosyl Donors that Display Reactivity, Selectivity, and Stability

Fluoropyridyl glycosides, synthesized from the corresponding glycosyl bromides, are shown to be excellent donors in glycosylation reactions. Both armed and disarmed donors were prepared and reacted smoothly with a series of glycosyl acceptors. Coupling pr

Cyanomethyl Ether as an Orthogonal Participating Group for Stereoselective Synthesis of 1,2-trans-β-O-Glycosides

Stereoselective formation of glycosidic linkages has been the prime focus for contemporary carbohydrate chemistry. Herein, we report cyanomethyl (CNMe) ether as an efficient and effective participating orthogonal protecting group for the stereoselective synthesis of 1,2-trans-β-O-glycosides. The participating group facilitated good to high β-selective glycosylation with a broad range of electron-rich and electron-deficient glycosyl acceptors. Detailed experimental and theoretical studies reveal the involvement of CNMe ether in the formation of a six-membered imine-type cyclic intermediate for the observed stereoselectivity. Rapid incorporation and selective removal of the CNMe ether group in the presence of benzyl ether and isopropylidene acetal protection have also been reported here. The nitrile group provided an opportunity for the glycodiversification through further derivatizations.

An Improved Procedure for Metallocene-Promoted Gylcosidation. Enhanced Reactivity by Employing 1:2 Ratio of Cp2HfCl2-AgClO4

Use of Cp2HfCl2-AgClO4 in 1:2 ratio rather than 1:1 ratio provides much higher raectivity for the activation of gylcosyl fluoride, where some implication for the involvement of Cp2Hf(ClO4)2 is obtained. β-Glucoside synthesis without resort to neighboring-

Investigation of α-Thioglycoside Donors: Reactivity Studies toward Configuration-Controlled Orthogonal Activation in One-Pot Systems

The influence of anomeric configuration upon thioglycoside donors remains relatively unexplored. Utilizing methodology developed for the stereoselective and high-yielding synthesis of α-glycosyl thiols, a series of α-thioglycosides were synthesized, and their reactivity was compared to that of their β-counterparts. The highly selective activation observed for anomeric pairs containing a 2-O-acyl moiety and additional findings are reported. Application of a pair of superarmed thioglycosides to a one-pot oligosaccharide system is also described, in which selectivity is a result of configuration-based orthogonal activation.

Stereoselective 1,2-cis-galactosylation assisted by remote neighboring group participation and solvent effects

Iodonium-ion promoted glycosylations in 1,4-dioxane/toluene with galactosyl donors having an electrondonating neighboring group participating functionality at C-4 give exceptional high α-anomeric selectivities.

Activation of glycoyl trihaloacetimidates with acid-washed molecular sieves in the glycosidation reaction

Figure presented Commercially available 4 A acid washed molecular sieves (4 A AW 300 MS) are efficient activators of glycosyl trichloro- and N-phenyltrifluoroacetimidates. These promoters allow glycosidation of primary and secondary saccharidic acceptors to be performed in high yield, under very mild conditions and by an experimentally simple procedure. In addition, the recyclability of such promoters also has been demonstrated.

Solvent and Other Effects on the Stereoselectivity of Thioglycoside Glycosidations

Iodonium-ion mediated glycosidation of thioglycosides in toluene/1,4-dioxane gives much higher α-selectivities than the use of conventional glycosylation solvents. Furthermore, it is shown that the iodonium-ion source, concentration and presence of molecu

Iodine: A versatile reagent in carbohydrate chemistry II. Efficient chemospecific activation of thiomethylglycosides

Iodine has been found to be an efficient promoter in the alcoholysis of unprotected or fully benzylated methyl 1-thio-β-D-galactopyranoside. Stereoselective formation of 1,2-cis linkages in oligosaccharide synthesis using 'armed' thiomethyl glycosides as