Thiodigalactoside

Base Information

• Chemical Name: Thiodigalactoside
• CAS No.: 51555-87-4
• Molecular Formula: C12H22O10S
• Molecular Weight: 358.36
• Hs Code.: 29389090
• Nikkaji Number: J586.952H
• Wikidata: Q76010100
• Metabolomics Workbench ID: 148851
• ChEMBL ID: CHEMBL52011
• Mol file: 51555-87-4.mol

Synonyms:galactopyranosyl 1-thio-beta-D-galactopyranoside;galactopyranosyl-1-thiogalactopyranoside;galactosyl-1-thio-beta-D-galactopyranoside;galactosyl-beta-D-thiogalactosylpyranoside;GalSGal;GBTGP;TDG cpd;thiodigalactoside;thiodigalactoside, (beta-D-Gal)-isomer;thiodigalactoside, (beta-D-galactopyranosyl)-isomer

Chemical Property of Thiodigalactoside

Chemical Property:

• PSA: 205.60000
• LogP: -4.68060
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly)
• XLogP3: -3.4
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 358.09336807
• Heavy Atom Count: 23
• Complexity: 353

Purity/Quality:

98%, ^*data from raw suppliers

TDG ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(C(O1)SC2C(C(C(C(O2)CO)O)O)O)O)O)O)O
• Isomeric SMILES: C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)S[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)O)O)O)O
• Description: Galectins are a family of glycan-binding lectins with diverse regulatory roles in physiological processes. They have significant roles in inflammation and cancer. Thiodigalactoside is a diglycan that binds galectins-1, -3, -8, and -9 with Kd values between 24 and 78 μM. It is used to investigate the roles of these galectins in cell signaling and carcinogenesis.
• Uses: Thiogdigalactosideis an inhibitor of galectin 1 which has an essential role in high-fat diet induced obesity development.

Technology Process of Thiodigalactoside

There total 3 articles about Thiodigalactoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (18968-44-0) → β-D-galactopyranosyl-(1→1)-1-thio-β-D-galactopyranoside (51555-87-4,80441-61-8)

Guidance literature:

With methanol; sodium methylate; at 20 ℃;

DOI:10.1016/j.carres.2019.107740

Reference yield:

2,3,4,6-tetra-O-acetyl-1-thio-D-galactopyranose (19879-84-6,56981-51-2,72541-16-3,72748-72-2,92691-83-3,110660-22-5,50615-66-2) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → β-D-galactopyranosyl-(1→1)-1-thio-β-D-galactopyranoside (51555-87-4,80441-61-8)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1016/S0008-6215(00)90766-3

Reference yield:

→ β-D-galactopyranosyl-(1→1)-1-thio-β-D-galactopyranoside (51555-87-4,80441-61-8)

Guidance literature:

Octa-O-acetyl-β-D-galactopyranosylmercapto-β-D-galactopyranosid, methanol.NaOCH3;

upstream raw materials:

2,3,4,6-tetra-O-acetyl-1-thio-D-galactopyranose

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

Refernces

• 1、 Di Gaetano, Sonia,Bedini, Emiliano,Landolfi, Alfredo,Pedone, Emilia,Pirone, Luciano,Saviano, Michele,Traboni, Serena,Capasso, Domenica,Iadonisi, Alfonso. "Synthesis of diglycosylated (di)sulfides and comparative evaluation of their antiproliferative effect against tumor cell lines: A focus on the nature of sugar-recognizing mediators involved". . . Retrieved 2019.