144781-45-3

Upstream product

• 87470-72-2 phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 71676-30-7 phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 
• 258286-51-0 phenyl (6-O-benzyl-2-O-benzoyl-1-thio-β-D-galactopyranoside) 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 496019-46-6 (2R,6S,7R,8S,8aS)-7,8-bis(benzyloxy)-2-phenyl-6-(phenylthio)hexahydropyrano[3,2-d][1,3]dioxine 
• 10257-28-0 D-Galactose 
• 124476-96-6 phenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 120095-47-8 phenyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 25878-60-8 D-galactose pentaacetate 

Relevant academic research and scientific papers

Total Synthesis of Trisaccharide Repeating Unit of O-Specific Polysaccharide of Pseudomonas fluorescens BIM B-582

The first total synthesis of the trisaccharide repeating unit of the O-specific polysaccharide of Pseudomonas fluorescens BIM B-582 is reported. This efficient synthesis involves consecutive 1,2-cis glycosylations including β-l-rhamnosylation and α select

Dimethyltin Dichloride Catalyzed Regioselective Alkylation of cis-1,2-Diols at Room Temperature

Here, we have developed a mild and general method for the regioselective installation of benzyl, allyl, para-methoxybenzyl and naphthyl groups on cis-1,2-diols. The optimized method operates at room temperature using dimethyltin dichloride as catalyst and

Directing effect by remote electron-withdrawing protecting groups at O-3 or O-4 position of donors in glucosylations and galactosylations

Glucosylations and galactosylations of various acceptors with donors possessing an electron-withdrawing benzylsulfonyl, benzoyl, or acetyl group at the O-3 or O-4 position were performed. A β-directing effect by the benzylsulfonyl group at O-3 of the glucosyl donors and by the benzylsulfonyl and acyl groups at O-4 of the glucosyl donors was observed. In contrast, acyl groups at O-3 of the glucosyl donors and acyl groups at O-3 and O-4 of the galactosyl donors exhibited an α-directing effect. The α-directing effect is partly considered to remote participation of the acyl groups, whereas the β-directing effect is somewhat attributed to the SN2-like reaction of the acceptor with the glycosyl triflate or the contact ion pair, which is stabilized by remote electron-withdrawing groups. Further evidence for the stability of the α-glycosyl triflates was determined by a low-temperature NMR study.

HClO4-silica-catalysed regioselective opening of benzylidene acetals and its application towards regioselective HO-4 glycosylation of benzylidene acetals in one-pot

Here we report a high-yielding method for the regioselective reductive ring opening of 4,6-O-benzylidene acetals of hexapyranosides using inexpensive and robust HClO4-SiO2 as the acidic catalyst and triethylsilane as the hydride dono

Single-step multisyntheses of glycosyl acceptors: Benzylation of n-1 hydroxyl groups of phenylthio glycosides of xylose, mannose, glucose, galactose, 2-azido-2-deoxy-glucose, and 2-azido-2-deoxy-galactose

An array of synthons is required to access an oligosaccharide library; however, multistep and thus time-consuming synthesis is inevitable. To rapidly access such synthetic units, multiple benzylation reactions of monosaccharides under phase-transfer condi

Chiral crown ethers based on galactopyranosides

The 1,4- and 1,6-bridged 20- and 23-membered galactocrown ethers 7, 8 and 11 were synthesized by intramolecular trans-glycosidation of the phenyl 1-thio-D-galactopyranosides 5, 6, and 10, respectively. The relevant precursors 5, 6, and 10 were obtained from phenyl 2,3,6-tri-O-benzyl-1-thio-β-D-galactopyranoside (2) and phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside (3), respectively, via two etherification steps. Compounds 2 and 3 are accessible from the same precursor, phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (1), by regioselective opening of benzylidene acetal. O-Alkylation of 2 and 3 with bis(2-chloroethyl)ether gave phenyl 2,3,6-tri-O-benzyl-4-[2-(2-chloro-ethoxy)ethyl]-1-thio-β-D- galactopyranoside (4) and phenyl 2,3,4-tri-O-benzyl-6-[2-(2-chloro-ethoxy)ethyl]-1-thio-β-D- galactopyranoside (9), respectively. The ensuing chain elongation of 4 was carried out with triethylene glycol and tetraethylene glycol, respectively, yielding 5 and 6. Compound 9 was alkoxylated with tetraethylene glycol under the same reaction conditions yielding phenyl 2,3,4-tri-O-benzyl-6-O-{2-[ω-hydroxy-penta-(oxyethylene) ethyl]}-1-thio-β-D-galactopyranoside (10). The yields of the chiral crowns 7, 8 and 11, obtained in the final cyclization step from the thioglycosides 5, 6, and 10, are 32-61%, i.e., they could be more than doubled compared to previous experiments with O-glycosidic precursors. High β-stereoselectivity was found for the cyclizations to the 1,4-bridged crowns 7 and 8. In contrast, the more flexible 6-O-polyethylene derivative 10 cyclized exclusively to the 1,6-bridged α-glycosidic crown ether 11.

Design and synthesis of new aminoglycoside antibiotics containing neamine as an optimal core structure: Correlation of antibiotic activity with in vitro inhibition of translation

The structure and activity of the pseudodisaccharide core found in aminoglycoside antibiotics was probed with a series of synthetic analogues in which the position of amino groups was varied around the glucopyranose ring. The naturally occurring structure