131564-36-8

Basic information

• Product Name: ethyl (S)-4,6-O-benzylidene-1-thio-β-D-galactopyranoside
• Synonyms: ethyl (S)-4,6-O-benzylidene-1-thio-β-D-galactopyranoside
• CAS NO: 131564-36-8
• Molecular Weight: 312.387
• Mol File: 131564-36-8.mol

Chemical Properties

• CAS DataBase Reference: ethyl (S)-4,6-O-benzylidene-1-thio-β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (S)-4,6-O-benzylidene-1-thio-β-D-galactopyranoside(131564-36-8)
• EPA Substance Registry System: ethyl (S)-4,6-O-benzylidene-1-thio-β-D-galactopyranoside(131564-36-8)

Safety Data

• Hazardous Substances Data: 131564-36-8(Hazardous Substances Data)

Upstream product

• 149563-08-6 (2R,4aR,6S,7R,8S,8aR)-6-(ethylthio)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diyl dibenzoate 
• 100-52-7 benzaldehyde 
• 604-69-3 β-D-glucose pentaacetate 
• 4163-60-4 β-D-galactose peracetate 
• 55722-49-1 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 851963-28-5 ethyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 56245-60-4 ethyl 1-thio-β-D-galactopyranoside 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 83-87-4 D-glucose pentaacetate 
• 492-61-5 β-D-glucose 
• 7473-36-1 ethyl 1-thio-β-D-glucopyranoside 

Downstream Products

• 151725-62-1 ethyl 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 136597-23-4 ethyl 3-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 197853-38-6 ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 149563-08-6 (2R,4aR,6S,7R,8S,8aR)-6-(ethylthio)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diyl dibenzoate 
• 201056-71-5 ethyl (5R)-4,6-O-benzylidene-1-thio-3-O-pivaloyl-β-D-glucopyranoside 
• 392675-28-4 ethyl 4,6-O-benzylidene-2,3-O-carbonate-1-thio-β-D-glucopyranoside 
• 889129-00-4 (2R,4aR,6S,7R,8S,8aR)-8-(benzyloxy)-6-(ethylthio)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl 4-oxopentanoate 
• 904689-98-1 ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-2-O-levulinoyl-1-thio-β-D-glucopyranoside 
• 904689-95-8 p-methoxyphenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 904689-93-6 p-methoxyphenyl 3-O-benzyl-4,6-O-benzylidene-2-O-levulinoyl-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 883556-88-5 ethyl 4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside 
• 1259036-14-0 ethylthio 3-O-(6-O-(2-(azidomethyl)benzoyl)-2-O-benzoyl-4-O-benzyl-3-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)-4,6-O-benzylidene-β-D-glucopyranoside 
• 1259036-08-2 ethylthio 4,6-O-benzylidene-2-O-(4,6-O-benzylidene-2,3-di-O-levulinyl-β-D-glucopyranosyl)-β-D-glucopyranoside 
• 1259035-91-0 ethylthio 4,6-O-benzylidene-3-O-(4,6-O-benzylidene-2,3-di-O-levulinyl-β-D-glucopyranosyl)-β-D-glucopyranoside 

Relevant articles and documents

Cu(OTf)2-catalyzed Et3SiH-reductive etherification of various carbonyl compounds with trimethylsilyl ethers

A triethylsilane-reductive etherification of the trimethylsilyl ethers with a variety of carbonyl compounds in good yields at room temperature employing 0.5 mol% Cu(OTf)2 as an extremely efficient catalyst is described here.

Acyclic tethers mimicking subunits of polysaccharide ligands: Selectin antagonists

We report on the design and synthesis of molecules having E- and P-selectins blocking activity both in vitro and in vivo. The GlcNAc component of the selectin ligand sialyl LewisX was replaced by an acyclic tether that links two saccharide units. The minimization of intramolecular dipole-dipole interactions and the gauche effect would be at the origin of the conformational bias imposed by this acyclic tether. The stereoselective synthesis of these molecules, their biochemical and biological evaluations using surface plasmon resonance spectroscopy (SPR), and in vivo assays are described. Because the structure of our analogues differs from the most potent E-selectin antagonists reported, our acyclic analogues offer new opportunities for chemical diversity.

Automated access to well-defined ionic oligosaccharides

Ionic polysaccharides are part of many biological events, but lack structural characterisation due to challenging purifications and complex synthesis. Four monosaccharides bearing modifications not found in nature are used for the automated synthesis of a collection of ionic oligosaccharides. Structural analysis reveals how the charge pattern affects glycan conformation.

One-Pot Relay Glycosylation

A novel one-pot relay glycosylation has been established. The protocol is characterized by the construction of two glycosidic bonds with only one equivalent of triflic anhydride. This method capitalizes on the in situ generated cyclic-thiosulfonium ion as the relay activator, which directly activates the newly formed thioglycoside in one pot. A wide range of substrates are well-accommodated to furnish both linear and branched oligosaccharides. The synthetic utility and advantage of this method have been demonstrated by rapid access to naturally occurring phenylethanoid glycoside kankanoside F and resin glycoside merremoside D.

Synthesis of Glucuronoxylan Hexasaccharides by Preactivation-Based Glycosylations

The synthesis of two glucuronoxylans is described, which both consist of a pentaxylan backbone and a glucuronic acid linked to the 2 position in the fourth xylose residue from the reducing end. The two target molecules differ in the 4 position of the glucuronic acid where one is unsubstituted while the other contains a methyl ether. The pentaxylan backbone is assembled in four glycosylation reactions with phenyl thioglycoside donors. The couplings are performed by preactivation of the donor with in-situ-generated p-nitrobenzenesulfenyl triflate prior to addition of the acceptor. The glucuronic acids are then attached by Koenigs-Knorr glycosylations followed by deprotections. The syntheses employ a total of 8 steps from monosaccharide building blocks and afford the two glucuronoxylans in 12 and 15 % overall yield. The hexasaccharide products are valuable substrates for investigating the activity and specificity of glucuronoxylan-degrading enzymes.

A versatile approach to the synthesis of mannosamine glycosides

O-Picoloyl protecting groups at remote positions can affect the stereoselectivity of glycosylation by means of the H-bond-mediated aglycone delivery (HAD) pathway. A new practical method for the stereoselective synthesis of β-glycosides of mannosamine is reported. The presence of the O-picoloyl group at the C-3 position of a mannosamine donor can provide high or complete stereocontrol. The method was also utilized for the synthesis of a biologically relevant trisaccharide related to the capsular polysaccharide of Streptococcus pneumoniae serotype 4. Also reported herein is a method to achieve complete α-manno stereoselectivity with mannosamine donors equipped with 3-O-benzoyl group. This journal is

Efficient one-pot per-: O -acetylation-thioglycosidation of native sugars, 4,6- O -arylidenation and one-pot 4,6- O -benzylidenation-acetylation of S -/ O -glycosides catalyzed by Mg(OTf)2

A sequential one-pot per-O-acetylation-S-/O-glycosidation of native mono and disaccharides under solvent free conditions using 0.5 mole% of Mg(OTf)2 as a non-hygroscopic, recyclable catalyst is reported. Regioselective 4,6-O-arylidenation of glycosides and thioglycosides with benzaldehyde or p-methoxybenzaldehyde dimethyl acetal is catalyzed by 10 mole% of Mg(OTf)2 to produce the corresponding 4,6-O-arylidenated product in high yields. Mg(OTf)2 can also mediate sequential one-pot benzylidenation-acetylation of mono and disaccharide based glycosides and thioglycosides in high yield.

A Sugar-Based Gelator for Marine Oil-Spill Recovery

Marine oil spills constitute an environmental disaster with severe adverse effects on the economy and ecosystem. Phase-selective organogelators (PSOGs), molecules that can congeal oil selectively from oil–water mixtures, have been proposed to be useful for oil-spill recovery. However, a major drawback lies in the mode of application of the PSOG to an oil spill spread over a large area. The proposed method of using carrier solvents is impractical for various reasons. Direct application of the PSOG as a solid, although it would be ideal, is unknown, presumably owing to poor dispersion of the solid through the oil. We have designed five cheap and easy-to-make glucose-derived PSOGs that disperse in the oil phase uniformly when applied as a fine powder. These gelators were shown to selectively congeal many oils, including crude oil, from oil–water mixtures to form stable gels, which is an essential property for efficient oil-spill recovery. We have demonstrated that these PSOGs can be applied aerially as a solid powder onto a mixture of crude oil and sea water and the congealed oil can then be scooped out. Our innovative mode of application and low cost of the PSOG offers a practical solution to oil-spill recovery.

High-yield total synthesis of (-)-strictinin through intramolecular coupling of gallates

This paper describes a total synthesis of (-)-strictinin, an ellagitannin that is 1-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl (HHDP)-β-d-glucose. In the study, total efficiency of the synthesis was improved to produce a 78% overall yield in 13 steps from d-glucose. In the synthesis, formation of the 4,6-(S)-HHDP bridge including the 11-membered bislactone ring was a key step, in which intramolecular aryl-aryl coupling was adopted. The coupling was oxidatively induced by CuCl2-n-BuNH2 with perfect control of the axial chirality, and the reaction conditions of this coupling were optimized thoroughly to achieve the quantitative formation of the bridge.

'Naked' and hydrated conformers of the conserved core pentasaccharide of N-linked glycoproteins and its building blocks

N-glycosylation of eukaryotic proteins is widespread and vital to survival. The pentasaccharide unit -Man3GlcNAc2- lies at the protein-junction core of all oligosaccharides attached to asparagine side chains during this process. Although its absolute conservation implies an indispensable role, associated perhaps with its structure, its unbiased conformation and the potential modulating role of solvation are unknown; both have now been explored through a combination of synthesis, laser spectroscopy, and computation. The proximal -GlcNAc-GlcNAc- unit acts as a rigid rod, while the central, and unusual, -Man-β-1,4-GlcNAc- linkage is more flexible and is modulated by the distal Man-α-1,3- and Man-α-1,6- branching units. Solvation stiffens the 'rod' but leaves the distal residues flexible, through a β-Man pivot, ensuring anchored projection from the protein shell while allowing flexible interaction of the distal portion of N-glycosylation with bulk water and biomolecular assemblies.