P-AMINOPHENYL-1-THIO-BETA-D-GLUCOPYRANOS IDE

Base Information

• Chemical Name: P-AMINOPHENYL-1-THIO-BETA-D-GLUCOPYRANOS IDE
• CAS No.: 58737-22-7
• Molecular Formula: C12H17NO5S
• Molecular Weight: 287.33
• Hs Code.: 29389090
• Mol file: 58737-22-7.mol

Synonyms:P-Aminophenyl-1-thio-beta-d-glucopyranoside;4-Aminophenyl 1-thio-β-D-glucopyranoside;4-Aminophenyl-β-D-thioglucopyranoside;4-Aminophenyl beta-D-thioglucopyranoside;

Chemical Property of P-AMINOPHENYL-1-THIO-BETA-D-GLUCOPYRANOS IDE

Chemical Property:

• Boiling Point: 586.5 °C at 760 mmHg
• Flash Point: 308.5 °C
• PSA: 141.47000
• Density: 1.54 g/cm³
• LogP: -0.25800
• Storage Temp.: −20°C

Purity/Quality:

98% ^*data from raw suppliers

4-Aminophenyl b-D-thioglucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Aminophenyl 1-Thio-β-D-glucopyranoside is a glycoside derivative of 4-Amino-benzenethiol (A591510); a compound used in the preparation of CCR5 antagonists as anti-HIV-1 agents. It can also be used to synthesize functionalized Coumarins (C755380) as acetylcholinesterase inhibitors.

Technology Process of P-AMINOPHENYL-1-THIO-BETA-D-GLUCOPYRANOS IDE

There total 3 articles about P-AMINOPHENYL-1-THIO-BETA-D-GLUCOPYRANOS IDE 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: 99.0%

4-aminotiophenol (1193-02-8) + 4-nitrophenyl-β-D-glucoside (2492-87-7) → (2S,3R,4S,5S,6R)-2-((4-aminophenyl)thio)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (58737-22-7,129970-93-0)

Guidance literature:

With E₁₅₉Q mutant of thioglycoligase from Dictyoglomus thermophilum; In aq. buffer; at 20 ℃; for 24h; pH=9; Reagent/catalyst; Temperature; Catalytic behavior; Enzymatic reaction;

DOI:10.1002/ejoc.202100672

Reference yield: 86.0%

1-thio-β-D-glucopyranose (22566-82-1,23558-19-2,49858-49-3,63073-99-4,135891-42-8,7534-35-2) + p-aminoiodobenzene (540-37-4) → (2S,3R,4S,5S,6R)-2-((4-aminophenyl)thio)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (58737-22-7,129970-93-0)

Guidance literature:

With pyridine; [nickel(II)dichloride(dimethoxyethane)]; zinc; In methanol; at 20 ℃; for 2h;

DOI:10.1002/chem.201302999

Reference yield:

→ (2S,3R,4S,5S,6R)-2-((4-aminophenyl)thio)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (58737-22-7,129970-93-0)

Guidance literature:

DOI:10.1016/S0008-6215(00)83329-7

upstream raw materials:

1-thio-β-D-glucopyranose

p-aminoiodobenzene

4-aminotiophenol

4-nitrophenyl-β-D-glucoside

Refernces

• 1、 Brachet, Etienne,Brion, Jean-Daniel,Alami, Mouad,Messaoudi, Samir. "Nickel-catalyzed arylation, alkenylation, and alkynylation of unprotected thioglycosides at room temperature". supporting information. p. 15276 - 15280. Retrieved 2013/11/06.