4-Nitrophenyl 3-O-(b-D-glucopyranosyl)-b-D-glucopyranoside

Base Information

• Chemical Name: 4-Nitrophenyl 3-O-(b-D-glucopyranosyl)-b-D-glucopyranoside
• CAS No.: 26255-70-9
• Molecular Formula: C₁₈H₂₅NO₁₃
• Molecular Weight: 463.395
• DSSTox Substance ID: DTXSID101201599
• Nikkaji Number: J2.044.208E
• Mol file: 26255-70-9.mol

Synonyms:26255-70-9;4-Nitrophenyl 3-O-(b-D-glucopyranosyl)-b-D-glucopyranoside;(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;beta-D-Glucopyranoside, 4-nitrophenyl 3-O-beta-D-glucopyranosyl-;4-Nitrophenyl3-O-(b-D-glucopyranosyl)-b-D-glucopyranoside;LBTDRWMZFQVCAR-GZQMJUEHSA-N;DTXSID101201599;p-Nitrophenyl ?-D-Laminaribioside;W-202115;4-Nitrophenyl 3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside;p-Nitrophenyl 3-O-beta-D-glucopyranosyl-beta-D-glucopyranoside;(2S,3R,4S,5S,6R)-2-(((2R,3R,4S,5R,6S)-3,5-Dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)tetrahydro-2H-pyran-4-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;(2S,3R,4S,5S,6R)-2-{[(2R,3R,4S,5R,6S)-3,5-DIHYDROXY-2-(HYDROXYMETHYL)-6-(4-NITROPHENOXY)OXAN-4-YL]OXY}-6-(HYDROXYMETHYL)OXANE-3,4,5-TRIOL

Chemical Property of 4-Nitrophenyl 3-O-(b-D-glucopyranosyl)-b-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 232-234°C dec.
• Storage Temp.: -20°C Freezer
• Solubility.: Water
• XLogP3: -2
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 6
• Exact Mass: 463.13258985
• Heavy Atom Count: 32
• Complexity: 612

Purity/Quality:

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

p-Nitrophenylβ-D-Laminaribioside ^*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)O)OC3C(C(C(C(O3)CO)O)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[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• Uses: p-Nitrophenyl β-D-Laminaribioside (cas# 26255-70-9) is a compound useful in organic synthesis.

Technology Process of 4-Nitrophenyl 3-O-(b-D-glucopyranosyl)-b-D-glucopyranoside

There total 24 articles about 4-Nitrophenyl 3-O-(b-D-glucopyranosyl)-b-D-glucopyranoside 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: 96.0%

1-deoxy-1-fluoro-α-D-glucose (2106-10-7) + 4-nitrophenyl-β-D-glucoside (2492-87-7) → 4-nitrophenyl β-D-glucopyranosyl-(1->3)-β-D-glucopyranoside (26255-70-9)

Guidance literature:

With E383A mutant β-glucosidase; In phosphate buffer; at 35 ℃; pH=7.0; Further Variations:; Temperatures; pH-values; concentration; Enzyme kinetics;

DOI:10.1016/j.carres.2006.04.049

Reference yield: 82.0%

p-nitrophenyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside (105600-45-1) → p-nitrophenyl 3-O-α-D-mannopyranosyl-α-D-mannopyranoside (26255-70-9,81562-04-1,81573-30-0,86021-56-9,110891-71-9,136632-95-6,147103-37-5,150301-00-1,93979-06-7)

Guidance literature:

With sodium methylate; In methanol; for 1h;

DOI:10.1016/S0008-6215(00)90315-X

Reference yield: 62.0%

Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-(4-nitro-phenoxy)-4-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester (195715-98-1) → 4-nitrophenyl β-D-glucopyranosyl-(1->3)-β-D-glucopyranoside (26255-70-9)

Guidance literature:

With sodium methylate; In methanol; for 7h; Ambient temperature;

upstream raw materials:

p-nitrophenyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside

p-nitrophenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranoside

2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide

p-nitrophenyl 2-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside

Downstream raw materials:

Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-(4-nitro-phenoxy)-4-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester

4-nitrophenyl β-D-glucopyranosyl-(1-4)-β-D-glucopyranosyl-(1-3)-β-D-glucopyranoside

C₄₄H₅₅NO₂₈

C₄₄H₅₅NO₂₈

Refernces

• 1、 Pozzo, Tania,Plaza, Merichel,Romero-Garcia, Javier,Faijes, Magda,Karlsson, Eva Nordberg,Planas, Antoni. "Glycosynthases from Thermotoga neapolitana β-glucosidase 1A: A comparison of α-glucosyl fluoride and in situ-generated α-glycosyl formate donors". . p. 132 - 139. Retrieved 2014/07/21.
• 2、 Wei, Jinhua,Lv, Xun,Lue, Yang,Yang, Gangzhu,Fu, Lifeng,Yang, Liu,Wang, Jianjun,Gao, Jianhui,Cheng, Shuihong,Duan, Qian,Jin, Cheng,Li, Xuebing. "Glycosynthase with broad substrate specificity-an efficient biocatalyst for the construction of oligosaccharide library". . p. 2414 - 2419. Retrieved 2013/05/23.