4'-Nitrophenyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranosid

Base Information

• Chemical Name: 4'-Nitrophenyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranosid
• CAS No.: 68667-01-6
• Molecular Formula: C20H23NO11S
• Molecular Weight: 485.469
• Mol file: 68667-01-6.mol

Synonyms:4-Nitrophenyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranosid

Chemical Property of 4'-Nitrophenyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranosid

Chemical Property:

• PSA: 185.55000
• LogP: 2.29320

Purity/Quality:

4'-NITROPHENYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4'-Nitrophenyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranosid

There total 10 articles about 4'-Nitrophenyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranosid 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: 90.0%

di(p-nitrophenyl) disulfide (100-32-3) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((4-nitrophenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (68667-01-6)

Guidance literature:

di(p-nitrophenyl) disulfide; With hydrogenchloride; triphenylphosphine; In toluene; at 70 ℃; for 0.75h;

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide; With tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; In water; toluene; at 20 ℃; Further stages.;

DOI:10.1080/07328300701410635

Reference yield: 87.0%

para-nitrobenzenethiol (1849-36-1) + β-D-glucose pentaacetate (604-69-3) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((4-nitrophenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (68667-01-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; Molecular sieve; Inert atmosphere;

DOI:10.1039/b813048e

Reference yield: 83.0%

para-nitrobenzenethiol (1849-36-1) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((4-nitrophenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (68667-01-6)

Guidance literature:

With tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; In ethyl acetate; for 20h;

DOI:10.1002/jms.880

upstream raw materials:

para-nitrobenzenethiol

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

tetraacetyl thioglucose

4-Fluoronitrobenzene

Downstream raw materials:

p-N-acetamidophenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-[(4-aminophenyl)thio]tetrahydro-2H-pyran-3,4,5-triyl triacetate

p-nitrophenyl 1-thio-β-D-glucopyranoside