2'-NITROPHENYL TETRA-O-ACETYL-A-D-GLUCOPYRANOSIDE

Base Information

• Chemical Name: 2'-NITROPHENYL TETRA-O-ACETYL-A-D-GLUCOPYRANOSIDE
• CAS No.: 35023-96-2
• Molecular Formula: C₂₀H₂₃NO₁₂
• Molecular Weight: 469.402
• Mol file: 35023-96-2.mol

Synonyms:Glucoside,a-o-nitrophenyl-, tetraacetate(4CI); o-Nitrophenyl 2,3,4,6-tetra-O-acetyl-a-D-glucopyranoside

Chemical Property of 2'-NITROPHENYL TETRA-O-ACETYL-A-D-GLUCOPYRANOSIDE

Chemical Property:

• Boiling Point: 555.0±50.0 °C(Predicted)
• PSA: 169.48000
• Density: 1.38±0.1 g/cm3(Predicted)
• LogP: 1.57990

Purity/Quality:

99% ^*data from raw suppliers

2'-NITROPHENYL TETRA-O-ACETYL-A-D-GLUCOPYRANOSIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2'-NITROPHENYL TETRA-O-ACETYL-A-D-GLUCOPYRANOSIDE

There total 3 articles about 2'-NITROPHENYL TETRA-O-ACETYL-A-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:

2-hydroxynitrobenzene (88-75-5,78813-12-4) + α-D-glucopyranose peracetylate (604-68-2) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (14581-85-2) + (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (35023-96-2)

Guidance literature:

With zinc(II) chloride;

DOI:10.1021/ja01255a060

Reference yield:

2-hydroxynitrobenzene (88-75-5,78813-12-4) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (14581-85-2) + (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (35023-96-2)

Guidance literature:

2-hydroxynitrobenzene; With 1-butyl-3-methylimidazolium chloride; silver(l) oxide; at 25 ℃; for 0.25h; Darkness; neat (no solvent);

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide; at 25 - 80 ℃; for 0.5h; optical yield given as %de; stereoselective reaction; Darkness; neat (no solvent);

DOI:10.1002/ejoc.201000188

Reference yield:

→ (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (35023-96-2)

Guidance literature:

Acetobromglucose, 1) 2-Nitrophenol, 2) Hg(CN)2, HgBr2 (80-100grad);

upstream raw materials:

2-hydroxynitrobenzene

α-D-glucopyranose peracetylate

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

Downstream raw materials:

o-nitrophenyl-α-D-galactopyranoside

Refernces