4-Aminophenyl alpha-D-mannopyranoside

Base Information

• Chemical Name: 4-Aminophenyl alpha-D-mannopyranoside
• CAS No.: 34213-86-0
• Molecular Formula: C12H17NO6
• Molecular Weight: 271.27
• Hs Code.: 29400090
• DSSTox Substance ID: DTXSID00187800
• Nikkaji Number: J415.964K
• Wikidata: Q27132347
• Metabolomics Workbench ID: 62568
• ChEMBL ID: CHEMBL1173631
• Mol file: 34213-86-0.mol

Synonyms:4-aminophenyl alpha-D-mannopyranoside;4-aminophenyl-alpha-D-mannoside;4-aminophenylmannoside;p-aminophenyl-alpha-D-mannopyranoside

Chemical Property of 4-Aminophenyl alpha-D-mannopyranoside

Chemical Property:

• Vapor Pressure: 3.43E-13mmHg at 25°C
• Melting Point: 165-166°C
• Refractive Index: 1.662
• Boiling Point: 555.9°Cat760mmHg
• PKA: 12.93±0.70(Predicted)
• Flash Point: 290°C
• PSA: 125.40000
• Density: 1.517g/cm³
• LogP: -0.97130
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble
• XLogP3: -1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 271.10558726
• Heavy Atom Count: 19
• Complexity: 283

Purity/Quality:

98%, ^*data from raw suppliers

4-Aminophenyl a-D-Mannopyranoside ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1N)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1N)O[C@@H]2[C@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Uses: Increases the uptake rate of liposomes.

Technology Process of 4-Aminophenyl alpha-D-mannopyranoside

There total 12 articles about 4-Aminophenyl alpha-D-mannopyranoside 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: 99.0%

4-nitrophenyl-α-D-mannopyranoside (10357-27-4) → p-aminophenyl-α-D-mannopyranoside (34213-86-0)

Guidance literature:

With hydrogen; palladium dihydroxide; In water; at 20 ℃; for 15h; atmospheric pressure;

DOI:10.1016/j.tet.2005.03.102

Reference yield:

1-O-p-nitrophenyl-2,3,4,6-tetra-O-acetyl α-D-mannopyranoside (13242-51-8) → p-aminophenyl-α-D-mannopyranoside (34213-86-0)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol / 2 h / 20 °C

2: 95 percent / Pd/C / methanol / 0.5 h / 20 °C

With sodium methylate; palladium on activated charcoal; In methanol;

DOI:10.1039/b008323m

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → p-aminophenyl-α-D-mannopyranoside (34213-86-0)

Guidance literature:

Multi-step reaction with 3 steps

1: BF₃*Et₂O / CH₂Cl₂ / 72 h / 20 °C

2: NaOMe / methanol / 2 h / 20 °C

3: 95 percent / Pd/C / methanol / 0.5 h / 20 °C

With boron trifluoride diethyl etherate; sodium methylate; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1039/b008323m

upstream raw materials:

4-nitrophenyl-α-D-mannopyranoside

1-O-p-nitrophenyl-2,3,4,6-tetra-O-acetyl α-D-mannopyranoside

4-nitro-phenol

D-Mannose pentaacetate

Downstream raw materials:

[p-isothiocyanato]-phenyl α-D-mannopyranoside

6-[3,4-dihydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid [4-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-amide

p-azidophenyl-α-D-mannopyranoside

4-Benzamidophenyl-α-D-mannopyranoside

Refernces

• 1、 Downs, Frederick J.,Carroll, Robert W.. "Nickel-charcoal as a catalyst for the synthesis of p-aminophenyl α-D-mannopyranoside and α-L-fucopyranoside". . p. 323 - 325. Retrieved 1981.
• 2、 -. "Brain-targeting nano liposome carrying positively charged polymer/miR-195 compound, and preparation method and application thereof". Paragraph 0085; 0090. . Retrieved 2020/06/30.
• 3、 Jayasundara, Dilushan R.,Duff, Thomas,Angione, M. Daniela,Bourke, Jean,Murphy, Deirdre M.,Scanlan, Eoin M.,Colavita, Paula E.. "Carbohydrate coatings via aryldiazonium chemistry for surface biomimicry". . p. 4122 - 4128. Retrieved 2013/11/19.