2-CHLORO-4-NITROPHENYL-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE

Base Information

• Chemical Name: 2-CHLORO-4-NITROPHENYL-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE
• CAS No.: 35023-71-3
• Molecular Formula: C20H22 Cl N O12
• Molecular Weight: 503.847
• Mol file: 35023-71-3.mol

Synonyms:2-Chloro-4-nitrophenyl2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside

Chemical Property of 2-CHLORO-4-NITROPHENYL-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 144-145°C
• Refractive Index: 1.55
• Boiling Point: 574.258oC at 760 mmHg
• Flash Point: 301.101oC
• PSA: 169.48000
• Density: 1.442g/cm3
• LogP: 2.23330
• Solubility.: Dichloromethane, Ethyl Acetate

Purity/Quality:

99%, ^*data from raw suppliers

2-Chloro-4-nitrophenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-Chloro-4-nitrophenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (cas# 35023-71-3) is a compound useful in organic synthesis.

Technology Process of 2-CHLORO-4-NITROPHENYL-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE

There total 8 articles about 2-CHLORO-4-NITROPHENYL-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE 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: 89.0%

2-chloro-4-nitrophenol (619-08-9) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2-chloro-4-nitrophenyl) 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (35023-71-3,153823-58-6)

Guidance literature:

With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; at 20 ℃; for 18h; stereoselective reaction;

DOI:10.1021/ol3023374

Reference yield: 65.2%

→ (2-chloro-4-nitrophenyl) 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (35023-71-3,153823-58-6)

Guidance literature:

In dichloromethane; at -25 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With boron trifluoride diethyl etherate; In dichloromethane; for 0.5h; Molecular sieve; Inert atmosphere;

Reference yield: 23.0%

2-chloro-4-nitrophenol (619-08-9) + C16H22O11*BrH → (2-chloro-4-nitrophenyl) 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (35023-71-3,153823-58-6)

Guidance literature:

With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; water; at 35 ℃; for 3h;

DOI:10.1016/j.jcat.2015.12.026

upstream raw materials:

2-chloro-4-nitrophenol

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

β-D-glucose pentaacetate

D-glucose pentaacetate

Downstream raw materials:

uridine diphosphate glucose

(2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime

(2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-gluco-hexodialdo-1,5-pyranose-6-O-methyloxime

(2-chloro-4-nitrophenyl) 2,3,4-tri-O-benzoyl-β-D-glucopyranoside

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