2-NITROPHENYL-ALPHA-D-GALACTOPYRANOSIDE

Base Information

• Chemical Name: 2-NITROPHENYL-ALPHA-D-GALACTOPYRANOSIDE
• CAS No.: 19887-85-5
• Molecular Formula: C₁₂H₁₅NO₈
• Molecular Weight: 301.253
• Hs Code.: 2932999099
• Mol file: 19887-85-5.mol

Synonyms:Galactopyranoside,o-nitrophenyl, a-D-(6CI,8CI); 2-Nitrophenyl a-D-galactopyranoside; o-Nitrophenyl a-D-galactopyranoside; o-Nitrophenyl a-D-galactoside

Chemical Property of 2-NITROPHENYL-ALPHA-D-GALACTOPYRANOSIDE

Chemical Property:

• Vapor Pressure: 6.1E-14mmHg at 25°C
• Boiling Point: 572.4 °C at 760 mmHg
• PKA: 12.69±0.70(Predicted)
• Flash Point: 300 °C
• PSA: 145.20000
• Density: 1.599 g/cm³
• LogP: -0.70330
• Storage Temp.: −20°C

Purity/Quality:

98%, ^*data from raw suppliers

o-Nitrophenylα-D-Galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: It is a specific substrate for α-D-Galactosidase.

Technology Process of 2-NITROPHENYL-ALPHA-D-GALACTOPYRANOSIDE

There total 10 articles about 2-NITROPHENYL-ALPHA-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:

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (3053-17-6) → o-nitrophenyl D-galactopyranoside (2816-24-2,18249-33-7,19710-96-4,19887-85-5,56193-44-3,81132-76-5,118014-27-0,118396-84-2,369-07-3)

Guidance literature:

With methanol; barium methoxide;

DOI:10.1021/ja01165a601

Reference yield:

→ o-nitrophenyl D-galactopyranoside (2816-24-2,18249-33-7,19710-96-4,19887-85-5,56193-44-3,81132-76-5,118014-27-0,118396-84-2,369-07-3)

Guidance literature:

DOI:10.1042/bj1330089

Reference yield:

2-hydroxynitrobenzene (88-75-5,78813-12-4) → o-nitrophenyl D-galactopyranoside (2816-24-2,18249-33-7,19710-96-4,19887-85-5,56193-44-3,81132-76-5,118014-27-0,118396-84-2,369-07-3)

Guidance literature:

Multi-step reaction with 2 steps

1: TBAHS; aq. Na₂CO₃ / CH₂Cl₂ / 3 h / 20 °C

2: NaOMe; MeOH

With methanol; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; In dichloromethane;

DOI:10.1016/j.bmcl.2005.12.010

upstream raw materials:

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

2-hydroxynitrobenzene

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

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

Downstream raw materials:

o-nitrophenyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside

Benzyl-4-O-(β-D-galactopyranosyl)-β-D-xylopyranosid

benzyl 3-O-(β-D-galactopyranosyl)-β-D-xylopyranoside

(2S,3R,4S,5R,6R)-2-((3R,4R,5R,6S)-4,5-Dihydroxy-6-phenoxy-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

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.
• 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.