p-nitrophenyl endo-2',3'-O-(1-methoxycarbonyl-o,o'-biphenylenemethylidene)ribofuranoside

Base Information

• Chemical Name: p-nitrophenyl endo-2',3'-O-(1-methoxycarbonyl-o,o'-biphenylenemethylidene)ribofuranoside
• CAS No.: 127179-71-9
• Molecular Formula: C₂₆H₂₁NO₉
• Molecular Weight: 491.454
• Mol file: 127179-71-9.mol

Synonyms:p-nitrophenyl endo-2',3'-O-(1-methoxycarbonyl-o,o'-biphenylenemethylidene)ribofuranoside

Chemical Property of p-nitrophenyl endo-2',3'-O-(1-methoxycarbonyl-o,o'-biphenylenemethylidene)ribofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrophenyl endo-2',3'-O-(1-methoxycarbonyl-o,o'-biphenylenemethylidene)ribofuranoside

There total 3 articles about p-nitrophenyl endo-2',3'-O-(1-methoxycarbonyl-o,o'-biphenylenemethylidene)ribofuranoside 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: 25.0%

9,9-dimethoxy-1-methoxycarbonylfluorene (116910-84-0) + 1-O-(p-Nitrophenyl)-β-D-ribofuranoside (59495-69-1) → p-nitrophenyl endo-2',3'-O-(1-methoxycarbonyl-o,o'-biphenylenemethylidene)ribofuranoside (127179-71-9)

Guidance literature:

With pyridinium p-toluenesulfonate; In 1,2-dichloro-ethane; Heating;

DOI:10.1021/ja00227a049

Reference yield: 25.0%

9,9-dimethoxy-1-methoxycarbonylfluorene (116910-84-0) + 1-O-(p-Nitrophenyl)-β-D-ribofuranoside (59495-69-1) → endo-2',3'-O-(1-methoxycarbonyl-o,o'-biphenylenemethylidene)-1',5'-cycloribofuranose (127086-69-5) + p-nitrophenyl endo-2',3'-O-(1-methoxycarbonyl-o,o'-biphenylenemethylidene)ribofuranoside (127179-71-9)

Guidance literature:

With pyridinium p-toluenesulfonate; In 1,2-dichloro-ethane; 1.) from RT to 55 deg C, 4 h, 2.) 55 deg C, 48 h;

Reference yield:

9-oxo-9H-fluorene-1-carboxylic acid (1573-92-8) → p-nitrophenyl endo-2',3'-O-(1-methoxycarbonyl-o,o'-biphenylenemethylidene)ribofuranoside (127179-71-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) p-toluenesulfonic acid / 1.) reflux, 2.) reflux, overnight

2: 25 percent / pyridinium tosylate / 1,2-dichloro-ethane / 1.) from RT to 55 deg C, 4 h, 2.) 55 deg C, 48 h

With pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; In 1,2-dichloro-ethane;

upstream raw materials:

9,9-dimethoxy-1-methoxycarbonylfluorene

1-O-(p-Nitrophenyl)-β-D-ribofuranoside

9-oxo-9H-fluorene-1-carboxylic acid

Downstream raw materials:

4-nitro-phenol

p-nitrophenyl endo-2',3'-O-(1-aminocarbonyl-o,o'-biphenylenemethylidene)ribofuranoside

Refernces

• 1、 Cherian, Xavier M.,Arman, Scott A. Van,Czarnik, Anthony W.. "Experimental Support for Asp-52's Importance in Lysozyme Using a Carbohydrate-Based Enzyme Model. Acetal Hydrolysis Catalyzed by a "Stereoelectronically Correct" Carboxylate Group". . p. 6566 - 6568. Retrieved 2007/10/02.