p-Nitrophenyl -D-Cellobioside Heptacetate

Base Information

• Chemical Name: p-Nitrophenyl -D-Cellobioside Heptacetate
• CAS No.: 69948-03-4
• Molecular Formula: C32H39NO20
• Molecular Weight: 757.64676
• Mol file: 69948-03-4.mol

Synonyms:p-Nitrophenyl -D-Cellobioside Heptacetate;p-Nitrophenyl β-D-Lactopyranoside Heptaacetate;4-Nitrophenyl 4-O-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside 2,3,6-Triacetate;4-Nitrophenyl 4-O-β-D-Glucopyranosyl-β-D-glucopyranoside Tetraacetate

Chemical Property of p-Nitrophenyl -D-Cellobioside Heptacetate

Chemical Property:

• PSA: 266.84000
• LogP: 1.11650
• Solubility.: Dichloromethane,

Purity/Quality:

97% ^*data from raw suppliers

4-Nitrophenyl b-D-cellobioside heptacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: p-Nitrophenyl β-D-Cellobioside Heptacetate (cas# 69948-03-4) is a compound useful in organic synthesis.

Technology Process of p-Nitrophenyl -D-Cellobioside Heptacetate

There total 3 articles about p-Nitrophenyl -D-Cellobioside Heptacetate 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: 44.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + Acetic acid (3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-bromo-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester (69308-57-2) → p-nitrophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside (69948-03-4)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; water; for 3h; Ambient temperature;

DOI:10.1016/S0008-6215(98)00294-8

Reference yield:

D-cellobiose octaacetate (5328-50-7,5346-90-7,6291-42-5,6920-00-9,20764-63-0,20880-60-8,20880-65-3,22352-19-8,23973-20-8,32447-69-1,34213-32-6,52554-32-2,53956-64-2,56907-29-0,56994-12-8,56994-13-9,57128-38-8,67650-36-6,68036-17-9,68036-19-1,78215-50-6,78215-51-7,79549-48-7,80446-82-8,85249-04-3,93221-83-1,93779-27-2,111407-83-1,111407-84-2,111407-85-3,120328-65-6,123809-59-6,132341-46-9,132341-47-0,132341-49-2,145307-94-4,3616-19-1) → p-nitrophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside (69948-03-4)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen bromide; acetic acid / dichloromethane / 0 - 20 °C

2: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water; dichloromethane / 20 °C

With hydrogen bromide; tetra(n-butyl)ammonium hydrogensulfate; acetic acid; sodium hydroxide; In dichloromethane; water;

DOI:10.1002/ejoc.201201507

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → p-nitrophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside (69948-03-4)

Guidance literature:

With zinc(II) chloride;

upstream raw materials:

4-nitro-phenol

Acetic acid (3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-bromo-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

D-cellobiose octaacetate

Downstream raw materials:

4-nitrophenyl β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside

4-nitrophenyl β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-cellobioside

4-nitrophenyl β-D-fucopyranosyl-(1→4)-β-D-cellobioside

p-aminophenyl β-cellobioside

Refernces

• 1、 Sangseethong, Kunruedee,Penner, Michael H.. "p-Aminophenyl β-cellobioside as an affinity ligand for exo-type cellulases". . p. 245 - 250. Retrieved 2007/10/03.