2-[6-[4,5-Dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Base Information

• Chemical Name: 2-[6-[4,5-Dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS No.: 106927-48-4
• Molecular Formula: C24H35 N O18
• Molecular Weight: 625.538
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID90399334
• Mol file: 106927-48-4.mol

Synonyms:106927-48-4;4-Nitrophenyl beta-D-cellotrioside;2-[6-[4,5-dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;4-Nitrophenyl b-D-cellotrioside;P-NITROPHENYL BETA-D-CELLOTRIOSIDE;4-Nitrophenyl |A-D-cellotrioside;DTXSID90399334;4-Nitrophenyl beta -D-cellotrioside;AKOS030255521;PD043795;Glc-beta1,4Glc-beta1,4Glc-beta1-O-PNP;FT-0672859

Chemical Property of 2-[6-[4,5-Dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 246-248°C dec.
• Refractive Index: 1.685
• Boiling Point: 971oC at 760 mmHg
• PKA: 12.43±0.70(Predicted)
• Flash Point: 541.1oC
• PSA: 303.50000
• Density: 1.75g/cm3
• LogP: -5.05490
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Water (Slightly)
• XLogP3: -4.7
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 9
• Exact Mass: 625.18541327
• Heavy Atom Count: 43
• Complexity: 889

Purity/Quality:

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

4-Nitrophenyl b-D-cellotrioside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])OC2C(C(C(C(O2)CO)OC3C(C(C(C(O3)CO)OC4C(C(C(C(O4)CO)O)O)O)O)O)O)O
• Uses: 4-Nitrophenyl β-D-cellotrioside is a chromogenic substrate for endoglucanases and cellobiohydrolases. Hydrolysis of this substrate by these enzymes liberates 4-nitrophenol, which generates a yellow color that is measured by monitoring absorbance at 405 nm.[Cayman Chemical] p-Nitrophenyl β-D-Cellotrioside (cas# 106927-48-4) is a compound useful in organic synthesis.

Technology Process of 2-[6-[4,5-Dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

There total 22 articles about 2-[6-[4,5-Dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol 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: 88.0%

p-nitrophenyl β-D-cellobioside (3482-57-3) + 1-deoxy-1-fluoro-α-D-glucose (2106-10-7) → 4-nitrophenyl β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside (106927-48-4) + 4-nitrophenyl β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-cellobioside (129411-62-7)

Guidance literature:

With Thermus nonproteolyticus HG₁₀₂ E₃₃₈A mutant; glycine; sodium hydroxide; In aq. buffer; at 45 ℃; for 48h; pH=8.8; Overall yield = 97 %; Enzymatic reaction;

DOI:10.1002/ejoc.201201507

Reference yield:

1-deoxy-1-fluoro-α-D-glucose (2106-10-7) → 4-nitrophenyl β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside (106927-48-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 38 percent / AbgGlu₃₅₈Ala, ammonium bicarbonate buffer / 8 h / Ambient temperature

2: 8 percent / AbgGlu₃₅₈Ala, ammonium bicarbonate buffer / 8 h / Ambient temperature

With AbgGlu₃₅₈Ala; ammonium bicarbonate buffer;

DOI:10.1021/ja980833d

Reference yield:

p-nitrophenyl β-D-cellobioside (3482-57-3) + 1-deoxy-1-fluoro-α-D-glucose (2106-10-7) → 4-nitrophenyl β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside (106927-48-4)

Guidance literature:

With rice BGlu1 β-glucosidase, E386G/Y341A/R178A mutant; In aq. buffer; at 30 ℃; for 24h; pH=7; Reagent/catalyst; Enzymatic reaction;

DOI:10.1002/pro.2556

upstream raw materials:

p-nitrophenyl β-D-cellobioside

1-deoxy-1-fluoro-α-D-glucose

4-nitrophenyl-β-D-glucoside

p-nitrophenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside

Downstream raw materials:

p-nitrophenyl β-D-cellobioside

4-nitro-phenol

cellotetraose

Refernces

• 1、 Codera, Victoria,Edgar, Kevin J.,Faijes, Magda,Planas, Antoni. "Functionalized Celluloses with Regular Substitution Pattern by Glycosynthase-Catalyzed Polymerization". . p. 1272 - 1279. Retrieved 2016/05/09.
• 2、 Mackenzie,Wang,Antony,Warren,Withers. "Glycosynthases: Mutant glycosidases for oligosaccharide synthesis [5]". . p. 5583 - 5584. Retrieved 2007/10/03.