3-Nitrophenyl b-D-galactopyranoside

Base Information

• Chemical Name: 3-Nitrophenyl b-D-galactopyranoside
• CAS No.: 3150-25-2
• Molecular Formula: C12H15NO8
• Molecular Weight: 301.253
• Hs Code.: 29389090
• European Community (EC) Number: 221-585-0
• DSSTox Substance ID: DTXSID801293757
• Nikkaji Number: J217.305K
• ChEMBL ID: CHEMBL49629
• Mol file: 3150-25-2.mol

Synonyms:3150-25-2;3-Nitrophenyl b-D-galactopyranoside;3-Nitrophenyl beta-D-galactopyranoside;3-NITROPHENYL-BETA-D-GALACTOPYRANOSIDE;(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(3-nitrophenoxy)oxane-3,4,5-triol;EINECS 221-585-0;m-Nitrophenyl beta-D-galactopyranoside;3-Nitrophenylb-D-galactopyranoside;CHEMBL49629;SCHEMBL869110;DTXSID801293757;MFCD00047517;3-Nitrophenyl I(2)-D-galactopyranoside;.beta.-D-Galactopyranoside, 3-nitrophenyl;Galactopyranoside, m-nitrophenyl, .beta.-D-;W-202299;(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(3-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property of 3-Nitrophenyl b-D-galactopyranoside

Chemical Property:

• Melting Point: 178-179 °C
• Boiling Point: 573.5 °C at 760 mmHg
• Flash Point: 300.6 °C
• PSA: 145.20000
• Density: 1.599 g/cm³
• LogP: -0.70330
• Storage Temp.: 2-8°C
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 301.07976644
• Heavy Atom Count: 21
• Complexity: 362

Purity/Quality:

98%, ^*data from raw suppliers

3-Nitrophenyl b-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)OC2C(C(C(C(O2)CO)O)O)O)[N+](=O)[O-]
• Isomeric SMILES: C1=CC(=CC(=C1)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)[N+](=O)[O-]

Technology Process of 3-Nitrophenyl b-D-galactopyranoside

There total 9 articles about 3-Nitrophenyl b-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: 83.0%

Tetra-O-acetyl-m-nitrophenyl-α-D-galactopyranosid (52571-64-9) → meta-nitrophenyl-α-D-galactopyranoside (3150-25-2,20838-44-2,28541-80-2,56140-66-0,72200-66-9,52571-71-8)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1021/acs.bioconjchem.8b00902

Reference yield:

D-galactose pentaacetate (25878-60-8) → meta-nitrophenyl-α-D-galactopyranoside (3150-25-2,20838-44-2,28541-80-2,56140-66-0,72200-66-9,52571-71-8)

Guidance literature:

Multi-step reaction with 3 steps

1: benzylamine / N,N-dimethyl-formamide / 20 °C

2: trifluorormethanesulfonic acid / -35 - 20 °C

3: sodium hydroxide / methanol

With trifluorormethanesulfonic acid; benzylamine; sodium hydroxide; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/acs.bioconjchem.8b00902

Reference yield:

2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate (74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,142831-80-9,127061-80-7) → meta-nitrophenyl-α-D-galactopyranoside (3150-25-2,20838-44-2,28541-80-2,56140-66-0,72200-66-9,52571-71-8)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluorormethanesulfonic acid / -35 - 20 °C

2: sodium hydroxide / methanol

With trifluorormethanesulfonic acid; sodium hydroxide; In methanol;

DOI:10.1021/acs.bioconjchem.8b00902

upstream raw materials:

meta-nitrophenol

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

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

β-D-galactose peracetate

Downstream raw materials:

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

methyl beta-D-galactopyranoside

Refernces

• 1、 Joachim, Ines,Rikker, Sebastian,Hauck, Dirk,Ponader, Daniela,Boden, Sophia,Sommer, Roman,Hartmann, Laura,Titz, Alexander. "Development and optimization of a competitive binding assay for the galactophilic low affinity lectin LecA from: Pseudomonas aeruginosa". . p. 7933 - 7948. Retrieved 2016/08/30.
• 2、 Sinnott,Souchard. "The mechanism of action of beta-galactosidase. Effect of aglycone nature and -deuterium substitution on the hydrolysis of aryl galactosides.". . p. 89 - 98. Retrieved 2007/10/04.