4-Nitrophenyl a-D-mannopyranoside

Base Information

• Chemical Name: 4-Nitrophenyl a-D-mannopyranoside
• CAS No.: 10357-27-4
• Molecular Formula: C12H15NO8
• Molecular Weight: 301.253
• Hs Code.: 29389090
• European Community (EC) Number: 233-776-6
• DSSTox Substance ID: DTXSID601299735
• Nikkaji Number: J236.785H
• Wikidata: Q27464496
• ChEMBL ID: CHEMBL1173567
• Mol file: 10357-27-4.mol

Synonyms:4'-nitrophenyl-alpha-D-mannopyranoside;4-nitrophenyl-alpha-D-mannopyranoside;alpha-PNM;p-nitrophenyl-alpha-mannoside;para-nitrophenyl-alpha-D-mannopyranoside;PNPAM

Chemical Property of 4-Nitrophenyl a-D-mannopyranoside

Chemical Property:

• Appearance/Colour: White-yellow crystal powder
• Melting Point: 179-181 °C
• Boiling Point: 582.2 °C at 760 mmHg
• PKA: 12.55±0.70(Predicted)
• Flash Point: 305.9 °C
• PSA: 145.20000
• Density: 1.599 g/cm³
• LogP: -0.70330
• Storage Temp.: 2-8°C
• Solubility.: DMF: 50 mg/mL, clear, very faintly yellow
• Water Solubility.: Soluble in water at 10mg/ml
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 301.07976644
• Heavy Atom Count: 21
• Complexity: 354

Purity/Quality:

98%, ^*data from raw suppliers

p-Nitrophenyl a-D-Mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1[N+](=O)[O-])O[C@@H]2[C@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Uses: p-Nitrophenyl α-D-Mannopyranoside (cas# 10357-27-4) is a compound useful in organic synthesis.

Technology Process of 4-Nitrophenyl a-D-mannopyranoside

There total 15 articles about 4-Nitrophenyl a-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: 95.0%

p-nitrophenyl 2,3,4,6-tetra-O-benzoyl-β-D-gulopyranoside (1262015-20-2) → p-nitrophenyl β-D-mannopyranoside (2492-87-7,3150-24-1,3767-28-0,5779-46-4,7493-95-0,7591-01-7,10357-27-4,35599-02-1,58800-28-5,64912-20-5,67672-67-7,67968-32-5,69967-94-8,89195-84-6)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃;

DOI:10.1016/j.carres.2010.10.001

Reference yield: 92.0%

4-nitrobenzyl tetra-O-pivaloyl-α-D-mannopyranoside (243120-94-7) → 4-nitrophenyl-α-D-mannopyranoside (10357-27-4)

Guidance literature:

With sodium methylate; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0008-6215(99)00065-8

Reference yield: 83.4%

1-O-p-nitrophenyl-2,3,4,6-tetra-O-acetyl α-D-mannopyranoside (13242-51-8) → 4-nitrophenyl-α-D-mannopyranoside (10357-27-4)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 5h; pH=Ca. 10;

upstream raw materials:

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

4-nitrobenzyl tetra-O-pivaloyl-α-D-mannopyranoside

4-nitro-phenol

D-Mannose pentaacetate

Downstream raw materials:

p-nitrophenyl 4,6-O-benzylidene-α-D-mannopyranoside

p-nitrophenyl 4,6-O-benzylidene-β-D-gulopyranoside

4-nitrophenyl-β-D-galactopyranoside

p-nitrophenyl 2-O-α-D-mannopyranosyl-α-D-mannopyranoside

Refernces

• 1、 Fairbanks, Antony J.,Qiu, Xin. "Direct Synthesis of para-Nitrophenyl Glycosides from Reducing Sugars in Water". . . Retrieved 2020.
• 2、 Nagase,Shinkai,Hamachi. "Post-photoaffinity labeling modification using aldehyde chemistry to produce a fluorescent lectin toward saccharide-biosensors". . p. 229 - 230. Retrieved 2001.
• 3、 -. "Brain-targeting nano liposome carrying positively charged polymer/miR-195 compound, and preparation method and application thereof". Paragraph 0085; 0089. . Retrieved 2020/06/30.