39483-51-7

Basic information

• Product Name: ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside
• Synonyms: ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside
• CAS NO: 39483-51-7
• Molecular Weight: 494.652
• Mol File: 39483-51-7.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside(39483-51-7)
• EPA Substance Registry System: ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside(39483-51-7)

Safety Data

• Hazardous Substances Data: 39483-51-7(Hazardous Substances Data)

Upstream product

• 171243-42-8 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 4356-77-8 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose 
• 10548-46-6 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose 
• 71117-16-3 2,3,4-tri-O-benzyl-β-D-glucopyranose 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glycopyranoside 
• 7473-36-1 (2R,3R,4S,5S,6R)-2-Ethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 3366-47-0 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose 
• 128850-49-7 ethyl 2,3,4-tri-O-benzyl-1-thio-6-O-(triphenylmethyl)-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 
• 152964-72-2 ethyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside 
• 157758-63-9 ethyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 65556-30-1 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 
• 142924-31-0 S-ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 

Downstream Products

• 83921-84-0 ethyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 39483-54-0 ethyl O-(2,3,4-tri-O-benzyl-6-O-p-nitrobenzyl-α-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 85011-43-4 ethyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 85011-42-3 ethyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 39604-21-2 [(2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-yl]-methanol 
• 1415590-56-5 ethyl 2,3,4-tri-O-benzyl-6-O-picolinyl-1-thio-α-D-glucopyranoside 
• 33639-75-7 2,3,4-tri-O-benzyl-6-deoxy-D-glucopyranose 
• 260779-96-2 ethyl 2,3,4-tri-O-benzyl-6-O-(tert-butoxycarbonylethanoyl)-1-thio-α-D-mannopyranoside 
• 262605-30-1 ethyl 2,3,4-tri-O-benzyl-6-O-(3-hydroxycarbonylpropanoyl)-1-thio-α-D-mannopyranoside 
• 543698-60-8 ethyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside 

Relevant articles and documents

A highly efficient and useful synthetic protocol for the cleavage of tert-butyldimethylsilyl (TBS) ethers using a catalytic amount of acetyl chloride in dry methanol

A wide variety of tert-butyldimethylsilyl (TBS) ethers as well as tert-butyldiphenylsilyl (TBDPS) ethers 1 can be easily deprotected to the corresponding parent hydroxyl compounds 2 by employing catalytic amounts of acetyl chloride in dry MeOH at 0°C to room temperature in good yields. Some of the major advantages are mild conditions, high efficiency, high selectivity, high yields, easy operation, and also compatibility with other protecting groups. Furthermore, no acetylation nor chlorination takes place under the experimental conditions.

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.

Rapid Synthesis of l-Idosyl Glycosyl Donors from α-Thioglucosides for the Preparation of Heparin Disaccharides

A new methodology for the synthesis of the most challenging heparin building block has been developed. Orthogonally protected l-idosyl glycosyl donors were prepared by C5 epimerization of the corresponding thioglucosides using the hydroboration/oxidation method followed by a 4,6-acetal formation. The α-anomeric configuration was crucial, and the bulky C4 substituent was advantageous for the high l-ido diastereoselectivity. The 4,6-arylmethylene group proved to be a directing element in glycosylation, whereby stereoselective α-idosylation could be achieved by using idosyl donors without a C-2 participating group.