196876-47-8

Upstream product

• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 

Downstream Products

• 196876-48-9 phenyl 2,4-di-O-acetyl-3-O-benzyl-6-O-cyanomethyl-1-thio-β-D-galactopyranoside 
• 362600-52-0 phenyl 3-O-benzyl-2,4,6-tri-O-pivaloyl-1-thio-β-D-galactopyranoside 
• 146920-71-0 phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-galactopyranoside 
• 124477-08-3 phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 196876-49-0 phenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 917568-40-2 phenyl 2-O-benzoyl-3,4-di-O-benzyl-1-thio-β-D-galactopyranoside 
• 917568-41-3 phenyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-D-galactopyranosiduronic acid 
• 917568-42-4 2-(trimethylsilyl)ethyl (phenyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-D-galactopyrosid) uronate 
• 917568-43-5 2-(trimethylsilyl)ethyl (phenyl 3,4-di-O-benzyl-2-O-benzoyl-1-thio-β-D-galactopyrosid) uronate S-oxide 
• 917568-60-6 phenyl [2-(trimethylsilyl)ethyl 3,4-di-O-benzyl-2-O-benzoyl-β-D-galactopyrosyluronate]-(1->4)-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside S-oxide 
• 917568-59-3 phenyl [2-(trimethylsilyl)ethyl 3,4-di-O-benzyl-2-O-benzoyl-β-D-galactopyrosyluronate]-(1->4)-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside 
• 362600-53-1 3-O-benzyl-2,4,6-tri-O-pivaloyl-α-D-galactopyranosyl fluoride 
• 362600-55-3 ethyl 6-(2,4,6-tri-O-acetyl-3-O-benzyl-β-D-galactopyranosyloxy)hexanoate 
• 362600-54-2 ethyl 6-(3-O-benzyl-2,4,6-tri-O-pivaloyl-β-D-galactopyranosyloxy)hexanoate 

Relevant academic research and scientific papers

Regioselective mono and multiple alkylation of diols and polyols catalyzed by organotin and its applications on the synthesis of value-added carbohydrate intermediates

A catalytic amount of dibutyltin dichloride was used to develop regioselective alkylation of diols and multiple alkylation of polyols. Alkyl groups, including allyl, alkynyl and long-chain alkyl groups, were successfully introduced to one or two hydroxyl

Regioselective benzylation of diols and polyols by catalytic amounts of an organotin reagent

An efficient one-pot method for the selective benzylation of diols and polyols using 0.1 equiv. of organotin reagents and tetrabutylammonium bromide as catalyst has been developed. The diols and polyols containing a cis-vicinal diol were regioselectively

MOENOMYCIN ANALOGS, METHODS OF SYNTHESIS, AND USES THEREOF

The present invention provides novel moenomycin analogs as well as pharmaceutical compositions thereof, methods of synthesis, and methods of use in treating an infection by administering an inventive compound to a subject in need thereof. The moenomycin a

The total synthesis of moenomycin A

Moenomycin A is the only known natural antibiotic that inhibits bacterial cell wall synthesis by binding to the transglycosylases that catalyze formation of the carbohydrate chains of peptidoglycan. We report here the total synthesis of moenomycin A using

Regioselective glycosylation of glucosamine and galactosamine derivates using O-pivaloyl galactosyl donors

Penta-O-pivaloyl-galactopyranose and tetra-O-pivaloyl-galactopyranosyl bromide after electrophilic activation reacted with 6-O-protected 2-azido-galactosides to give the precursor structures of the Thomsen-Friedenreich antigen disaccharide with high regioselectivity, but low yield. With 4,6-O-benzylidene protected 2-azidogalactosides and 2-O-pivaloyl phenylthio galactosides, T-antigen disaccharides of this type were obtained in good yields. Glycosylation reactions of 4,6-O-benzylidene protected glucosamine derivatives with O-pivaloyl protected galactosyl bromide efficiently gave lactolactosamine disaccharides. Even a thioglycoside was efficiently galactosylated by this method resulting in the formation of a disaccharide thioglycoside useful itself as a potential glycosyl donor.

De-O-benzylation of sterically hindered benzyl ethers

Sterically hindered benzyl ethers that cannot be removed by hydrogenolysis with a variety of catalysts are removed readily by the reaction with N-bromo-succinimide and light in the presence of aqueous calcium carbonate, a reaction developed by Binkley and Hehemann. It was found that these conditions are compatible with the presence of phthalimides and glycosyl sulfides and fluorides, in addition to the groups previously shown to be inert.

Synthetic studies on glycosphingolipids from the parasite Echinococcus multilocularis

Novel neutral glycosphingolipids isolated from the metacestodes of Echinococcus multilocularis by Persat, may be expected to be involved in host-parasite interactions. We have synthesized these glycosphingolipid analogues containing 2-branched fatty alkyl residues in place of ceramide. The glycosylation of galactosyl donors 4 and 5 with each of the acceptors 2 and 11 in the presence of N-iodosuccinimide (NIS)/TfOH, and the glycosylation of fucosyl donor 13 with acceptors 12 and 20 in the presence of dimethyl(methylthio)sulfonium triflate (DMTST) gave the desired oligosaccharide derivatives at good yield. The fully per-O-acylated 2-(trimethylsilyl)ethyl glycosides 6, 15, 21, and 26 were converted to glycosylimidates 7, 16, 22, and 27, which were condensed with 2-(tetradecyl)hexadecanol and subsequently deacylated give four target glycosphingolipid analogues. Copyright (C) 1999 Elsevier Science Ltd.

Generation of molecular diversity on N-acetyllactosamine via O-cyanomethyl ethers

The ability to generate molecular diversity around a natural carbohydrate ligand taking advantage of the rich chemistry of the nitrile functional group was demonstrated by synthesizing 24 derivatives of N-acetyllactosamine (LacNAc). The disaccharides prepared carried carboxymethyl, amidinomethyl, aminoethyl, and carbamoylmethyl substituents projecting from each of the six OH groups. The resulting LacNAc derivatives present new structural features with either negatively charged, positively charged, or polar-neutral small substituents sampling the entire periphery of the molecule. These new derivatives should be useful probes for studying carbohydrate-protein interactions in general, and for designing inhibitors of N-acetyllactosamine-binding proteins in particular.