126461-54-9

Usage

Uses

Used in Organic Chemistry Research:
Ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside is used as a protecting group for the hydroxyl groups of glucose in various chemical reactions. Its presence helps prevent unwanted side reactions, ensuring the selective functionalization of specific sites on the glucose molecule.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, Ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside is used as a key intermediate in the synthesis of glycosides. Glycosides are important compounds in medicinal chemistry, as they possess a wide range of biological activities and are used in the development of various drugs.
Used in Carbohydrate-based Molecule Synthesis:
Due to its reactivity and stability, Ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside serves as a valuable building block in the creation of complex carbohydrate-based molecules. These molecules have potential applications in various fields, including drug discovery, diagnostics, and materials science.

Upstream product

• 128850-49-7 ethyl 2,3,4-tri-O-benzyl-1-thio-6-O-(triphenylmethyl)-α-D-mannopyranoside 
• 157758-63-9 ethyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 32934-24-0 S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 316188-11-1 ethyl 6-O-[(tert-butyl)diphenylsilyl]-1-thio-α-D-mannopyranoside 
• 128643-87-8 ethyl 1-thio-6-O-(triphenylmethyl)-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 1415590-58-7 ethyl 2,3,4-tri-O-benzyl-6-O-picolinyl-1-thio-β-D-glucopyranoside 
• 7473-36-1 ethyl 1-thio-β-D-glucopyranoside 
• 197853-41-1 ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 20701-61-5 ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 144368-77-4 ethyl 2,3,4-tri-O-benzyl-1-thio-6-O-(triphenylmethyl)-β-D-glucopyranoside 
• 152964-70-0 ethyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside 
• 128850-48-6 ethyl 1-thio-6-O-triphenylmethyl-α-D-mannopyranoside 
• 218937-71-4 ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 

Downstream Products

• 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 
• 866322-01-2 ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-α-D-thiomannopyranoside 
• 283147-88-6 (2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxymethyl)-6-ethylsulfanyl-tetrahydro-pyran 
• 283177-70-8 C₆₃H₆₈O₁₀S 
• 543698-61-9 ethyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 260780-00-5 phenyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-1-thio-β-D-glucopyranoside 3,6'-malonate 
• 260779-98-4 ethyl 2,3,4-tri-O-benzyl-6-O-[(2-O-benzoyl-4,6-O-benzylidene-1-phenylthio-β-D-glucopyranos-3-yloxy)carbonylethanoyl]-1-thio-α-D-mannopyranoside 
• 260779-99-5 ethyl 2,3,4-tri-O-benzyl-6-O-[(2-O-benzoyl-6-O-benzyl-1-phenylthio-β-D-glucopyranos-3-yloxy)carbonylethanoyl]-1-thio-α-D-mannopyranoside 
• 128850-51-1 ethyl 2,3,4-tri-O-benzyl-6-O-dibenzyloxyphosphoryl-1-thio-α-D-mannopyranoside 
• 128643-88-9 Ethyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 150592-17-9 tert-Butyl-diphenyl-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane 
• 195192-50-8 ethyl 6-O-benzoyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Chiral acidic amino acids as tethers for intramolecular glycosylation

Intramolecular glycosylation with peptides as tethers is attractive for the synthesis of oligosaccharides because conjugation between the amino acids present in the tethers is facile. However, few studies have been published about the effects of the amino

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.

Picoloyl protecting group in synthesis: Focus on a highly chemoselective catalytic removal

The picoloyl ester (Pico) has proven to be a versatile protecting group in carbohydrate chemistry. It can be used for the purpose of stereocontrolling glycosylations via an H-bond-mediated Aglycone Delivery (HAD) method. It can also be used as a temporary protecting group that can be efficiently introduced and chemoselectively cleaved in the presence of practically all other common protecting groups used in synthesis. Herein, we will describe a new method for rapid, catalytic, and highly chemoselective removal of the picoloyl group using inexpensive copper(ii) or iron(iii) salts. This journal is

Studies on the substrate specificity of a GDP-mannose pyrophosphorylase from Salmonella enterica

A series of methoxy and deoxy derivatives of mannopyranose-1-phosphate (Manp-1P) were chemically synthesized, and their ability to be converted into the corresponding guanosine diphosphate mannopyranose (GDP-Manp) analogues by a pyrophosphorylase (GDP-ManPP) from Salmonella enterica was studied. Evaluation of methoxy analogues demonstrated that GDP-ManPP is intolerant of bulky substituents at the C-2, C-3, and C-4 positions, in turn suggesting that these positions are buried inside the enzyme active site. Additionally, both the 6-methoxy and 6-deoxy Manp-1P derivatives are good or moderate substrates for GDP-ManPP, thus indicating that the C-6 hydroxy group of the Manp-1P substrate is not required for binding to the enzyme. When taken into consideration with other previously published work, it appears that this enzyme has potential utility for the chemoenzymatic synthesis of GDP-Manp analogues, which are useful probes for studying enzymes that employ this sugar nucleotide as a substrate.

A simple and useful synthetic protocol for selective deprotection of tert-butyldimethylsilyl (TBS) ethers

A wide variety of tert-butyldimethylsilyl ethers 1 can be easily cleaved to the corresponding parent hydroxyl compound 2 in the presence of 5 mol % of acetonyltriphenylphosphonium bromide (ATPB) at room temperature. In addition, tert-butyldiphenylsilyl ethers can also be cleaved by using 20 mol % of the same catalyst. Alkyl tert-butyldimethylsilyl ethers can be deprotected to the hydroxyl compounds chemoselectively in the presence of aryl tert- butyldimethylsilyl ethers. Some of the major advantages are mild reaction conditions, no aqueous workup, high efficiency and chemoselectivity and compatibility with other protecting groups; no brominations occur in the aromatic ring under these experimental conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

A catalytic amount of nickel(II) chloride hexahydrate and 1,2-ethanedithiol is a good combination for the cleavage of tetrahydropyranyl (THP) and tert-butyldimethylsilyl (TBS) ethers

Various THP and TBS ethers can be unmasked easily to the corresponding hydroxyl compounds in good yields by using a combination of a catalytic amount of nickel(II) chloride hexahydrate and 1,2-ethanedithiol at room temperature. In addition, alkyl TBS ethers can be hydrolyzed chemoselectively in the presence of aryl TBS ethers. Moreover, alkyl TBS ethers can be cleaved easily in the presence of alkyl or aryl THP ethers using the same conditions.

First total synthesis of a GPI-anchored peptide

A GPI-anchored dipeptide of sperm CD52 antigen was prepared through a convergent synthesis. First, the dipeptide with its C-terminus free and the GPI with its nonreducing end phosphoeth-anolamine bearing a free amino group were synthesized separately. Then, the two building blocks were coupled with use of EDC/HOBt as the condensation reagent. Finally, the GPI-anchored peptide was deprotected to give the target molecule 1.

A Highly Efficient and Chemoselective Synthetic Protocol for Tetrahydropyranylation/Depyranylation of Alcohols and Phenols

Various alcohols and phenols can be converted efficiently to the corresponding tetrahydropyranyl (THP) ethers in good yields using catalytic amounts of bromodimethylsulfonium bromide (0.005-0.02 equivalent) at room temperature. On the other hand, various THP ethers can also be deprotected to the parent alcoholic or phenolic compounds in CH2Cl2/ MeOH (5:2) by employing 0.05 equivalent of the same catalyst. Some of the major advantages of this procedure are its mild conditions, that it is highly selective and efficient, high yielding, and cost-effective, that it needs no solvent and is compatible with the presence of other protecting groups. Furthermore, no brominations occur at a double or triple bond, at an allylic position or even at an aromatic ring. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

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.

Peptide templated glycosylation reactions

Glycosyl donors and acceptors may be covalently linked to aspartic acid residues via OH-6 esters. Peptide elaboration allows glycosylation reactions to be performed between donors and acceptors linked to this peptide template. These reactions display increased regio- and stereoselectivities, which are dependent on the nature of the peptide. Simple molecular modelling is used to rationalise the differing product distributions obtained by variation of the linking amino acid sequence. Copyright (C) 2000 Elsevier Science Ltd.