4-NITROPHENYL-BETA-L-FUCOPYRANOSIDE

Base Information

• Chemical Name: 4-NITROPHENYL-BETA-L-FUCOPYRANOSIDE
• CAS No.: 22153-71-5
• Molecular Formula: C12H15NO7
• Molecular Weight: 285.254
• Hs Code.: 29400090
• European Community (EC) Number: 244-808-3
• DSSTox Substance ID: DTXSID001262940
• Nikkaji Number: J208.783I
• Wikidata: Q27162431
• Mol file: 22153-71-5.mol

Synonyms:Galactopyranoside,p-nitrophenyl 6-deoxy-, β-L- (8CI);p-Nitrophenyl β-L-fucopyranoside;p-Nitrophenyl β-L-fucoside;p-Nitrophenyl-β-fucopyranoside;

Chemical Property of 4-NITROPHENYL-BETA-L-FUCOPYRANOSIDE

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 1.9E-11mmHg at 25°C
• Refractive Index: 1.623
• Boiling Point: 515.4 °C at 760 mmHg
• PKA: 12.68±0.70(Predicted)
• Flash Point: 265.5 °C
• PSA: 124.97000
• Density: 1.503 g/cm³
• LogP: 0.32430
• Storage Temp.: −20°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 285.08485182
• Heavy Atom Count: 20
• Complexity: 339

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Nitrophenyl b-L-fucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2=CC=C(C=C2)[N+](=O)[O-])O)O)O
• Isomeric SMILES: C[C@H]1[C@H]([C@H]([C@@H]([C@H](O1)OC2=CC=C(C=C2)[N+](=O)[O-])O)O)O
• Uses: 4-Nitrophenyl beta-L-Fucopyranoside is a chromogenic substrate for β-D-Fucosidase, producing a yellow solution upon cleavage.

Technology Process of 4-NITROPHENYL-BETA-L-FUCOPYRANOSIDE

There total 12 articles about 4-NITROPHENYL-BETA-L-FUCOPYRANOSIDE 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: 63.6%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 2,3,4‐tri‐O‐acetyl-α-L‐rhamnopyranosyl chloride (5160-09-8) → p-nitrophenyl α-L-rhamnopyranoside (1226-39-7,10231-84-2,18918-31-5,22153-71-5,33095-26-0,73351-15-2,74032-91-0,140387-70-8)

Guidance literature:

With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; at 30 ℃; for 4.5h; Reagent/catalyst;

DOI:10.1080/07328303.2017.1390578

Reference yield:

4-nitrophenyl-2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranoside (18992-37-5) → p-nitrophenyl α-L-rhamnopyranoside (1226-39-7,10231-84-2,18918-31-5,22153-71-5,33095-26-0,73351-15-2,74032-91-0,140387-70-8)

Guidance literature:

With methanol; sodium methylate;

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → p-nitrophenyl α-L-rhamnopyranoside (1226-39-7,10231-84-2,18918-31-5,22153-71-5,33095-26-0,73351-15-2,74032-91-0,140387-70-8)

Guidance literature:

Multi-step reaction with 2 steps

1: zinc chloride / 120 °C / unter vermindertem Druck

2: sodium methylate; methanol

With methanol; sodium methylate; zinc(II) chloride;

upstream raw materials:

4-nitrophenyl-2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranoside

4-nitro-phenol

2,3,4‐tri‐O‐acetyl-α-L‐rhamnopyranosyl chloride

p-nitrophenyl 2,3,4-tri-O-acetyl-β-L-fucopyranoside

Downstream raw materials:

1-(4-aminophenoxy)-α-L-rhamnopyranoside

p-aminophenyl-β-L-fucopyranoside

p-Nitrophenyl 3,4-O-isopropylidene-β-L-fucoside

p-nitrophenyl 3-O-methyl-β-L-fucopyranoside

Refernces

• 1、 Liu, Nianping,Tian, Xiangguang,Ding, Zekun,Zhou, Yongda,Zhang, Wan,Wang, Qingbing,Zhang, Yi,Gu, Yijun,Zhang, Jianbo. "Synthesis of aryl α-O-L-rhamnopyranoside by two-step reaction in one pot". . p. 220 - 234. Retrieved 2017/11/10.
• 2、 Morales, Juan Carlos,Zurita, Dacil,Penades, Soledad. "Carbohydrate-carbohydrate interactions in water with glycophanes as model systems". . p. 9212 - 9222. Retrieved 2007/10/03.