naphthalen-2-yl 2,3,4,6-tetra-O-acetyl-1-thiohexopyranoside

Base Information

• Chemical Name: naphthalen-2-yl 2,3,4,6-tetra-O-acetyl-1-thiohexopyranoside
• CAS No.: 7464-38-2
• Molecular Formula: C24H26O9S
• Molecular Weight: 490.5228
• Mol file: 7464-38-2.mol

Synonyms:

Chemical Property of naphthalen-2-yl 2,3,4,6-tetra-O-acetyl-1-thiohexopyranoside

Chemical Property:

• Vapor Pressure: 9.62E-14mmHg at 25°C
• Boiling Point: 586.6°C at 760 mmHg
• Flash Point: 289.5°C
• Density: 1.33g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of naphthalen-2-yl 2,3,4,6-tetra-O-acetyl-1-thiohexopyranoside

There total 5 articles about naphthalen-2-yl 2,3,4,6-tetra-O-acetyl-1-thiohexopyranoside 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: 98.0%

2-Naphthalenethiol (91-60-1) + β-D-galactose peracetate (4163-60-4) → 2-naphthyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (7464-38-2)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 4h;

DOI:10.1021/ol990406k

Reference yield: 91.0%

2-Naphthalenethiol (91-60-1) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → 2-naphthyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (7464-38-2)

Guidance literature:

With tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; In ethyl acetate; at 20 ℃; Inert atmosphere;

DOI:10.1039/c3ob41422a

Reference yield: 89.0%

2-Naphthalenethiol (91-60-1) + β-D-galactose peracetate (4163-60-4) → 2-naphthyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (7464-38-2) + C24H26O9S

Guidance literature:

With boron trifluoride diethyl etherate; at 20 ℃; for 1h; Ionic liquid;

DOI:10.1080/07328303.2011.605195

upstream raw materials:

2-Naphthalenethiol

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

β-D-galactose peracetate

bis(2-naphthyl)disulfide

Downstream raw materials:

2-naphthyl 3-(3-(aniline)-2-propyn-1-hydroxyl)-1-thio-β-D-galactopyranoside

2-naphthyl 3-(3-phenyl-1-hydroxy)-1-thio-β-D-galactopyranoside

1,5-anhydro-D-galactitol

Refernces

• 1、 Rodrigue, Jacques,Ganne, Geraldine,Blanchard, Bertrand,Saucier, Catherine,Giguere, Denis,Shiao, Tze Chieh,Varrot, Annabelle,Imberty, Anne,Roy, Rene. "Aromatic thioglycoside inhibitors against the virulence factor LecA from Pseudomonas aeruginosa". . p. 6906 - 6918. Retrieved 2013/10/08.
• 2、 Santra, Abhishek,Sau, Abhijit,Misra, Anup Kumar. "Synthesis of thioglycosides in room temperature ionic liquid". experimental part. p. 85 - 93. Retrieved 2012/01/03.