20701-61-5

Basic information

• Product Name: Ethyl 4,6-O-benzylidene-1-thio-b-D-glucopyranoside
• Synonyms: Ethyl 4,6-O-benzylidene-1-thio-b-D-glucopyranoside;Ethyl 4,6-O-benzylidene-beta-D-thioglucopyranoside;Ethyl 4,6-O-benzylidene-b-D-thioglucopyranoside;Ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside
• CAS NO: 20701-61-5
• Molecular Formula: C₁₅H₂₀O₅S
• Molecular Weight: 312.3813
• Mol File: 20701-61-5.mol
• Article Data: 24

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ethyl 4,6-O-benzylidene-1-thio-b-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 4,6-O-benzylidene-1-thio-b-D-glucopyranoside(20701-61-5)
• EPA Substance Registry System: Ethyl 4,6-O-benzylidene-1-thio-b-D-glucopyranoside(20701-61-5)

Safety Data

• Hazardous Substances Data: 20701-61-5(Hazardous Substances Data)

Usage

Uses

Ethyl 4,6-O-Benzylidene-b-D-thioglucopyranoside can be used for various organic synthesis.

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 7473-36-1 ethyl 1-thio-β-D-glucopyranoside 
• 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 
• 604-69-3 β-D-glucose pentaacetate 
• 100-52-7 benzaldehyde 
• 149563-08-6 (2R,4aR,6S,7R,8S,8aR)-6-(ethylthio)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diyl dibenzoate 

Downstream Products

• 136597-23-4 ethyl 3-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 887699-78-7 (2R,3R,4S,5R,6S)-6-Ethylsulfanyl-2-hydroxymethyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol 
• 887699-82-3 1-S-ethyl 2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-glucopyranoside 
• 887699-80-1 1-S-ethyl 2,3-di-O-(4-methoxybenzyl)-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-glucopyranoside 
• 887699-83-4 1-S-ethyl 2,3-di-O-(2-naphthylmethyl)-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-glucopyranoside 
• 152964-70-0 ethyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside 
• 39483-51-7 ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 141263-02-7 ethyl 2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 152964-73-3 ethyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 

Relevant articles and documents

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.

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.