125411-99-6

Basic information

• Product Name: 1-S-Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside
• Synonyms: 1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside;1-S-Ethyl 2,3,4,6-tetra-o-benzyl-beta-d-thiogalactopyranoside;Ethyl 2,3,4,6-tetrakis-O-(phenylmethyl)-1-thio-beta-D-galactopyranoside;1-S-Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside;Ethyl 2,3,4,6-tetra-O-benzyl-β-D-thiogalactopyranoside;Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside
• CAS NO: 125411-99-6
• Molecular Formula: C₃₆H₄₀O₅S
• Molecular Weight: 584.7648
• Mol File: 125411-99-6.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 691.2±55.0 °C(Predicted)
• Appearance: /
• Density: 1.19±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-S-Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 1-S-Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside(125411-99-6)
• EPA Substance Registry System: 1-S-Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside(125411-99-6)

Safety Data

• Hazardous Substances Data: 125411-99-6(Hazardous Substances Data)

Usage

Description

1-S-Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside, with the CAS number 125411-99-6, is a synthetic compound derived from the modification of a galactopyranoside structure. It is characterized by the presence of an ethyl group at the 1-S position and benzyl groups at the 2, 3, 4, and 6 positions. 1-S-Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside is known for its role in the synthesis of complex carbohydrate structures, particularly disaccharides and oligosaccharides.

Uses

Used in Carbohydrate Chemistry:
1-S-Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside is used as a synthetic intermediate for the preparation of disaccharides and oligosaccharides. Its application is based on its ability to undergo stereoselective 3,3-difluoroxindole-catalyzed regenerative glycosylation, which is a key step in the synthesis of these complex carbohydrate structures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-S-Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside is used as a key building block for the development of glycoconjugate drugs. These drugs have potential applications in various therapeutic areas, including cancer, infectious diseases, and autoimmune disorders, due to their ability to target specific cellular receptors and modulate immune responses.
Used in Research and Development:
1-S-Ethyl 2,3,4,6-tetra-O-benzyl-b-D-thiogalactopyranoside is also utilized in academic and industrial research settings for the investigation of carbohydrate-based drug candidates and the development of novel synthetic methods for carbohydrate chemistry. Its unique structural features make it a valuable tool for exploring the properties and functions of complex carbohydrates in biological systems.

Upstream product

• 100-39-0 benzyl bromide 
• 7473-36-1 ethyl 1-thio-β-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 75-08-1 ethanethiol 
• 121-43-7 Trimethyl borate 
• 1083195-70-3 3,4,6-tri-O-benzyl-2-O-(o-bromobenzyl)-1-thio-β-D-glucopyranose 
• 7732-18-5 water 
• 56245-60-4 ethyl 1-thio-β-D-galactopyranoside 
• 55722-49-1 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 101966-50-1 2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-galactopyranosyl fluoride 
• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 
• 85982-88-3 1-O-trimethylsilyl-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 530-26-7 D-Mannose 
• 83-87-4 β-D-mannopyranose pentaacetate 

Downstream Products

• 108739-69-1 methyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 108739-68-0 methyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 56822-48-1 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl acetate 
• 56822-49-2 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 173395-54-5 (1R,2S,6S,7R,8R)-4,4-Dimethyl-7-((3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3,5,9,11-tetraoxa-tricyclo[6.2.1.0^2,6]undecane 
• 171503-76-7 dicyclohexylmethyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 
• 197164-88-8 dicyclohexylmethyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-α-D-glucopyranoside 
• 216859-55-1 ethyl 2,3,4,6-tetra-O-benzyl-S-(N-tosylimino)-1-thio-β-D-glucopyranoside 
• 127840-88-4 1-thioethylhepta-o-benzoyl-β-D-maltose 

Relevant articles and documents

Anomeric Thioglycosides Give Different Anomeric Product Distributions under NIS/TfOH Activation

The reaction of a series of anomeric thioglycosides with various glycosyl acceptors and N-iodosuccinimide/catalytic triflic acid was investigated with respect to reactivity and anomeric selectivity. In general, β-configured donors were found to give a more β-selective reaction outcome compared to their α-configured counterparts. The relative reactivity of various thioglycosides was measured through competition experiments, and the following order was established: phenyl, tolyl, methyl, ethyl, isopropyl, and 1-adamantyl.

Regio- and stereoselective glycosylation of 2-(o-dihydroxyborylbenzyl) thioglucoside and unprotected methyl glycosides

A highly regio- and stereoselective glycosylation of a boronic acid-containing thioglucoside and unprotected methyl glycosides is described. A boronic acid moiety was installed at the ortho-position of the 2-O-benzyl group of a thioglucosyl donor. This provides transient partial protection for the unprotected glycosyl acceptor upon condensation and concomitantly prearranged the acceptor with respect to the donor for the ensuing intramolecular glycosylation.

Preparation method of clostridium bolteae surface capsular polysaccharide structure derivative

The invention discloses a preparation method of a clostridium bolteae surface capsular polysaccharide structure derivative and belongs to the field of sugar chemistry. The preparation method comprisesthe following steps: taking glucose as a glycosyl donor to obtain a target beta-glycosidic bond; then successfully synthesizing a disaccharide building block through an oxidization-reduction glucoseC-2 site method; then synthesizing a target oligosaccharide structure which takes the disaccharide building block as a repeating unit, such as the gram-positive bacterium surface capsular polysaccharide structure derivative [arrow3]-alpha-D-Manp-(1arrow4)-beta-D-Rhap-(1arrow]5-Linker. A reducing end of decaose is connected with a connecting arm and is used for connecting protein to form a glycoconjugate for carrying out immunology researches. The method provided by the invention has the advantages of simplicity, time saving, labor saving and low cost; the obtained clostridium bolteae surface capsular polysaccharide structure derivative is possibly used for developing and preparing medicine related to autism.