4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside

Base Information

• Chemical Name: 4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside
• CAS No.: 14131-42-1
• Molecular Formula: C20H23 N O12
• Molecular Weight: 469.402
• DSSTox Substance ID: DTXSID00535564
• Nikkaji Number: J730.214B
• Wikidata: Q72495825
• Mol file: 14131-42-1.mol

Synonyms:14131-42-1;4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside;p-Nitrophenyl-2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside;[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(4-nitrophenoxy)oxan-2-yl]methyl acetate;alpha-D-Glucopyranoside, 4-nitrophenyl, 2,3,4,6-tetraacetate;4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-a-D-glucopyranoside;(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(4-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate;p-Nitrophenyl-2,3,4,6-Tetra-O-acetyl-?-D-glucopyranoside;SCHEMBL7051328;DTXSID00535564;p-Nitrophenyl 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside;Allyltetraisopropylphosphorodiamidite;[(2R,3R,4S,5R,6R)-3,4,5-TRIS(ACETYLOXY)-6-(4-NITROPHENOXY)OXAN-2-YL]METHYL ACETATE;AKOS022180280;p-nitrophenyl alpha-d-glucopyranoside tetraacetate;W-201212;a-D-Glucopyranoside,4-nitrophenyl,2,3,4,6-tetraacetate;4-Nitrophenyl2,3,4,6-tetra-O-acetyl-a-D-glucopyranoside;p-Nitrophenyl alpha-D-Glucopyranoside 2,3,4,6-Tetraacetate;4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-I+/--D-glucopyranoside;p-Nitrophenyl-2,3,4,6-tetra-O-acetyl- alpha -D-glucopyranoside

Chemical Property of 4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside

Chemical Property:

• Melting Point: 110-114°C
• Boiling Point: 559.3±50.0 °C(Predicted)
• PSA: 169.48000
• Density: 1.38±0.1 g/cm3(Predicted)
• LogP: 1.57990
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 11
• Exact Mass: 469.12202517
• Heavy Atom Count: 33
• Complexity: 742

Purity/Quality:

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

4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC2=CC=C(C=C2)[N+](=O)[O-])OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC2=CC=C(C=C2)[N+](=O)[O-])OC(=O)C)OC(=O)C)OC(=O)C
• Uses: p-Nitrophenyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (cas# 14131-42-1) is a compound useful in organic synthesis.

Technology Process of 4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside

There total 35 articles about 4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-alpha-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: 99.0%

acetic anhydride (108-24-7) + 4-nitrophenyl-β-D-galactopyranoside (3150-24-1) → 4-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (2872-66-4,5987-78-0,13242-51-8,14131-42-1,17042-39-6,30902-95-5,40269-27-0,58918-67-5,67672-66-6,67968-31-4,72002-91-6,76549-82-1,89195-78-8,89195-79-9)

Guidance literature:

With pyridine; for 5h; cooling;

DOI:10.1002/chem.200305042

Reference yield: 95.0%

acetic anhydride (108-24-7) + 4-nitrophenyl-α-D-glucopyranoside (3767-28-0) → p-nitrophenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (14131-42-1)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 16h;

DOI:10.1016/j.bmcl.2011.02.062

Reference yield: 93.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → 4-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (2872-66-4,5987-78-0,13242-51-8,14131-42-1,17042-39-6,30902-95-5,40269-27-0,58918-67-5,67672-66-6,67968-31-4,72002-91-6,76549-82-1,89195-78-8,89195-79-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile;

DOI:10.1055/s-1998-1717

upstream raw materials:

4-nitro-phenol

β-D-glucose pentaacetate

α-D-glucopyranose peracetylate

2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose

Downstream raw materials:

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-aminophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

2,3,4,6-tetraacetylglucose

β-D-galactose peracetate

C₃₄H₄₀N₄O₁₀

Refernces

• 1、 -. "Nitrogen-containing aromatic ring derivative containing galactose and application thereof". . . Retrieved 2021/06/09.
• 2、 Ota, Ryo,Okamoto, Yumi,Vavricka, Christopher J.,Oka, Takuji,Matsunaga, Emiko,Takegawa, Kaoru,Kiyota, Hiromasa,Izumi, Minoru. "Chemo-enzymatic synthesis of p-nitrophenyl β-D-galactofuranosyl disaccharides from Aspergillus sp. fungal-type galactomannan". . p. 99 - 103. Retrieved 2019/01/16.