Thiodigalactoside

Base Information

• Chemical Name: Thiodigalactoside
• CAS No.: 80441-61-8
• Molecular Formula: C₁₂H₂₂O₁₀S
• Molecular Weight: 358.367
• Nikkaji Number: J586.952H
• Wikidata: Q76010100
• Metabolomics Workbench ID: 148851
• ChEMBL ID: CHEMBL52011
• Mol file: 80441-61-8.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:

• Vapor Pressure: 1.85E-23mmHg at 25°C
• Boiling Point: 712.6°Cat760mmHg
• Flash Point: 384.7°C
• PSA: 0.00000
• Density: 1.77g/cm³
• LogP: 0.00000
• 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:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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

Technology Process of Thiodigalactoside

There total 29 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: 95.0%

2,3,4,2′,3′,4′-hexa-O-benzyl-1-thio-α,α-D-trehalose → 1-thio-α,α-trehalose (17317-98-5,18977-84-9,68667-06-1,68778-86-9,68778-87-0,68778-88-1,108392-13-8,62853-32-1,80441-61-8)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethanol; ethyl acetate; at 20 ℃; for 48h;

DOI:10.1055/s-0036-1591595

Reference yield: 90.0%

6-O-acetyl-2,3,4,2′,3′,4′,6′-hepta-O-benzyl-1-thio-α,α-D-trehalose (1393083-67-4) → 1-thio-α,α-trehalose (17317-98-5,18977-84-9,68667-06-1,68778-86-9,68778-87-0,68778-88-1,108392-13-8,62853-32-1,80441-61-8)

Guidance literature:

6-O-acetyl-2,3,4,2′,3′,4′,6′-hepta-O-benzyl-1-thio-α,α-D-trehalose; With ammonia; sodium; In tetrahydrofuran; at -78 ℃; for 0.75h;

With ammonium chloride; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2012.05.159

Reference yield: 37.0%

D-Glucose (2280-44-6) + sodium salt of 1-thio-α-D-glucopyranose (62778-20-5) → 1-thio-α,β-trehalose (68778-86-9,80441-61-8) + 1-thio-α,α-trehalose (17317-98-5,18977-84-9,68667-06-1,68778-86-9,68778-87-0,68778-88-1,108392-13-8,62853-32-1,80441-61-8) + D-glycopyranosyl β-D-thioglucopyranoside (108392-13-8,80441-61-8)

Guidance literature:

In hydrogen fluoride; at 20 ℃;

DOI:10.1016/0008-6215(91)84116-V

upstream raw materials:

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

D-Glucose

sodium salt of 1-thio-α-D-glucopyranose

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

Downstream raw materials:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glucopyranoside

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 2019/07/12.
• 2、 Zeng, Xiaojun,Smith, Raymond,Zhu, Xiangming. "Synthesis of thioglycoside analogues of maradolipid". . p. 4165 - 4170. Retrieved 2013/05/23.