127061-10-3

Upstream product

• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 108-98-5 thiophenol 
• 73-34-7 6-deoxy-L-galactose 
• 30571-58-5 L-fucose tetraacetate 
• 7732-18-5 water 
• 6696-41-9 alpha-L-fucose 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-β-L-fucopyranose 
• 64913-16-2 L-fucose tetraacetate 

Downstream Products

• 187233-24-5 phenyl 6-deoxy-1-thio-β-L-galactopyranoside 
• 912478-19-4 phenyl 2,3-O-(2',3'-dimethoxy-2',3'-dimethylbutane)-1-thio-β-L-fucopyranoside 
• 912478-23-0 phenyl 2,3-O-(2',3'-dimethoxy-2',3'-dimethylbutane)-1-thio-β-L-quinovopyranoside 
• 162118-38-9 (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 
• 167612-35-3 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 
• 183875-25-4 phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside 
• 215364-17-3 phenyl 1-oxo-3,4-O-isopropylidene-1-thio-α-L-fucopyranoside 
• 196397-59-8 phenyl 3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 
• 196397-58-7 phenyl 3,4-O-isopropylidene-1-thio-α-L-fucopyranoside 

Relevant academic research and scientific papers

Synthesis of all eight stereoisomeric 6-deoxy-l-hexopyranosyl donors - Trends in using stereoselective reductions or mitsunobu epimerizations

The synthesis of all eight rare but biologically important 6deoxy-L-hexoses as their thioglycoside glycosyl donors starting from the commercially available L-rhamnose or L-fucose is reported. The synthesis of all eight 6-deoxy-L-hexoses was accomplished u

Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride

This study describes a new convenient method for the photocatalytic generation of glycosyl fluorides using sulfur(VI) hexafluoride as an inexpensive and safe fluorinating agent and 4,4′-dimethoxybenzophenone as a readily available organic photocatalyst. This mild method was employed to generate 16 different glycosyl fluorides, including the substrates with acid and base labile functionalities, in yields of 43%-97%, and it was applied in continuous flow to accomplish fluorination on an 7.7 g scale and 93% yield.

METHOD FOR PREPARING 2'-O-FUCOSYLLACTOSE

The present invention relates to a method for preparing 2'-O-fucosyllactose and to the protected fucosyl donor of the formula (I) used in this method. The method comprises reacting the fucose derivative of the formula (I) below with the compound of the ge

From disulfide- to thioether-linked glycoproteins

(Chemical Presented) Strengthening the bond: The introduction of a thiol tag in combination with chemoselective ligation to form a disulfide-linked bioconjugate is a selective and useful method for site-selective protein glycosylation. The phosphine-mediated desulfurization of such glycoconjugates to their reductant-resistant thioether-linked counterparts completes a convergent, site-selective synthesis of thioether-linked glycoproteins (see scheme).

Sonochemistry: A powerful way of enhancing the efficiency of carbohydrate synthesis

Using sonication as a means of facilitating organic reactions in carbohydrate chemistry was explored under the conditions used for traditional organic synthesis. An array of representative reactions, including hydroxy group manipulation (acylation, protection/deprotection, acyl group migration), thioglycoside synthesis, azidoglycoside synthesis, 1,3-dipolar cycloaddition and reductive cleavage of benzylidene, commonly used in the synthesis of carbohydrate derivatives was examined. A series of glycosylation reactions that employ thioglycosides, glycosyl trichloroacetimidate, glycosyl bromide and glycosyl acetate as the glycosyl donors was also examined. Our results demonstrate that sonication can significantly shorten the reaction time, enhance the reactivity of reactant and lead to superior yield and excellent stereoselectivity. More importantly, a general protocol of glycosylation may finally be developed. Sonication is compatible to the conditions used for traditional organic synthesis. We believe that sonication can also be applied to other areas of synthetic processes.

A mild and convenient indium(III) chloride-catalyzed synthesis of thioglycosides

The efficiency of glycosidation reactions generally involves a high chemical yield, as well as high/complete stereo- and regioselectivity. All these depend on the compatibility of the reactivity of glycosyl donors and acceptors. Among glycosyl donors, thi

Stereoselective synthesis of carba- and C-glycosyl analogs of fucopyranosides

Fucopyranoside analogs with methylene groups instead of endo- or exo- anomeric oxygens, carba- and C-fucopyranosides, respectively, were synthesized. For the synthesis of 5a-carba-L-fucose (1) two approaches were studied, which shared a common cyclitol bu

Combinatorial library of moenomycin analogs and methods of producing same

A combinatorial chemical library of compounds structurally related to the moenomycin class of antibiotics has the formula wherein D is a donor mono- or disaccharide, A is an acceptor monosaccharide, and P-R is a lipophosphoglycerate mimetic group. Members

Sulfinyl hexose derivatives useful for glycosylation

Hexose derivatives are described which facilitate control over the stereochemistry of the glycosyl bond formed in the course of a solid phase glycosylation reaction. Methods for their use are also described.

STUDIES DIRECTED TOWARD THE TOTAL SYNTHESIS OF POLYCAVERNOSIDE A. ENANTIOSELECTIVE SYNTHESIS OF THE DISACCHARIDE COMPONENT

Adaptation of the Mukaiyama-Nicolaou protocol to the coupling of a monounprotected thioglycoside to a glycosyl fluoride is capable of delivering the unusual disaccharide present in the title toxin.