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

Base Information

• Chemical Name: 2'-NITROPHENYL TETRA-O-ACETYL-A-D-GALACTOPYRANOSIDE
• CAS No.: 24624-80-4
• Molecular Formula: C20H23 N O12
• Molecular Weight: 469.402
• Mol file: 24624-80-4.mol

Synonyms:Galactopyranoside,o-nitrophenyl, 2,3,4,6-tetraacetate, a-D- (8CI)

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

Chemical Property:

• Melting Point: 169-170 °C
• Boiling Point: 555.0±50.0 °C(Predicted)
• PSA: 169.48000
• Density: 1.38±0.1 g/cm3(Predicted)
• LogP: 1.57990

Purity/Quality:

95% ^*data from raw suppliers

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

There total 4 articles about 2'-NITROPHENYL TETRA-O-ACETYL-A-D-GALACTOPYRANOSIDE 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: 51.0%

sodium o-nitrophenate (824-39-5) + 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl chloride (572-10-1,4451-35-8,4451-36-9,14227-52-2,14227-87-3,14227-88-4,14257-40-0,17081-03-7,19186-60-8,57237-01-1,65982-17-4,65982-18-5,65982-19-6,66966-08-3,144299-57-0) → (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (24624-80-4)

Guidance literature:

In N,N,N,N,N,N-hexamethylphosphoric triamide; 40 deg C, 6 h; r.t.;

Reference yield:

D-galactose pentaacetate (25878-60-8) → (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (24624-80-4)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethyl methyl ether, boron trifluoride

2: 51 percent / hexamethylphosphoric acid triamide / 40 deg C, 6 h; r.t.

With Dichloromethyl methyl ether; boron trifluoride; In N,N,N,N,N,N-hexamethylphosphoric triamide;

Reference yield:

2-hydroxynitrobenzene (88-75-5,78813-12-4) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (3053-17-6) + (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (24624-80-4)

Guidance literature:

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

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside; at 25 - 80 ℃; for 0.5h; optical yield given as %de; stereoselective reaction; Darkness; neat (no solvent);

DOI:10.1002/ejoc.201000188

upstream raw materials:

2-hydroxynitrobenzene

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

sodium o-nitrophenate

2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl chloride

Downstream raw materials:

o-nitrophenyl-α-D-galactopyranoside

Refernces

• 1、 Apparu, Maecel,Blanc-Muesser, Michele,Defaye, Jacques,Driguez, Hugues. "STEREOSELECTIVE SYNTHESES OF O- AND S-NITROPHENYL GLYCOSIDES. PART III. SYNTHESES IN THE &α-D-GALACTOPYRANOSE AND &α-MALTOSE SERIES". . p. 314 - 320. Retrieved 2007/10/02.