beta-D-Galactopyranoside, 2-nitrophenyl, 2,3,4,6-tetraacetate

Base Information

• Chemical Name: beta-D-Galactopyranoside, 2-nitrophenyl, 2,3,4,6-tetraacetate
• CAS No.: 3053-17-6
• Molecular Formula: C20H23NO12
• Molecular Weight: 469.402
• Nikkaji Number: J2.177.087F
• Mol file: 3053-17-6.mol

Synonyms:3053-17-6;beta-D-Galactopyranoside, 2-nitrophenyl, 2,3,4,6-tetraacetate;O-Nitrophenyl 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranoside;[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(2-nitrophenoxy)oxan-2-yl]methyl acetate;2-Nitrophenyl 2,3,4,6-tetra-O-acetyl-b-D-galactopyranoside;2-Nitrophenyl2,3,4,6-tetra-O-acetyl-b-D-galactopyranoside;O-Nitrophenyl 2,3,4,6-Tetra-O-acetyl-?-D-galactopyranoside;o-nitrophenyl-2,3,4,6-tetraacetyl-I(2)-D-galactopyranoside;1-O-(2-Nitrophenyl)-beta-D-galactopyranose 2,3,4,6-tetraacetate

Chemical Property of beta-D-Galactopyranoside, 2-nitrophenyl, 2,3,4,6-tetraacetate

Chemical Property:

• Vapor Pressure: 2.33E-12mmHg at 25°C
• Melting Point: 180-182°C
• Refractive Index: 1.54
• Boiling Point: 555 °C at 760 mmHg
• Flash Point: 204.6 °C
• PSA: 169.48000
• Density: 1.38 g/cm³
• LogP: 1.57990
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• 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: 750

Purity/Quality:

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

2-Nitrophenyl 2,3,4,6-tetra-O-acetyl-b-D-galactopyranoside ^*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=CC=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=CC=C2[N+](=O)[O-])OC(=O)C)OC(=O)C)OC(=O)C
• Uses: O-Nitrophenyl 2,3,4,6-Tetra-O-acetyl-β-D-galactopyranoside (cas# 3053-17-6) is a compound useful in organic synthesis.

Technology Process of beta-D-Galactopyranoside, 2-nitrophenyl, 2,3,4,6-tetraacetate

There total 6 articles about beta-D-Galactopyranoside, 2-nitrophenyl, 2,3,4,6-tetraacetate 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) + o-nitrophenyl D-galactopyranoside (2816-24-2,18249-33-7,19710-96-4,19887-85-5,56193-44-3,81132-76-5,118014-27-0,118396-84-2,369-07-3) → (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (3053-17-6)

Guidance literature:

With pyridine; for 5h; cooling;

DOI:10.1002/chem.200305042

Reference yield: 94.0%

2-hydroxynitrobenzene (88-75-5,78813-12-4) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (3053-17-6)

Guidance literature:

2-hydroxynitrobenzene; With C₁₆H₂₈AgN₄⁽¹⁺⁾; N-benzyl-N,N,N-triethylammonium chloride; at 25 ℃; for 0.333333h;

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside; at 25 ℃; for 3h;

DOI:10.1016/j.carres.2011.03.007

Reference yield: 81.0%

acetobromogalactose (572-09-8,3068-32-4,4026-32-8,6919-96-6,13242-53-0,14227-54-4,14795-18-7,19186-59-5,21698-13-5,29907-26-4,53369-42-9,60619-58-1,61303-35-3,67337-79-5,69127-37-3,70749-15-4,72002-90-5,75247-30-2,75880-74-9,78418-57-2,102339-89-9,102339-90-2,103530-40-1,114028-03-4,114718-45-5,138514-70-2,138514-71-3,19285-38-2) + 2-hydroxynitrobenzene (88-75-5,78813-12-4) → (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (3053-17-6)

Guidance literature:

In acetonitrile; at 20 ℃; for 3h; Inert atmosphere; Molecular sieve;

upstream raw materials:

2-hydroxynitrobenzene

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

acetic anhydride

o-nitrophenyl D-galactopyranoside

Downstream raw materials:

o-aminophenyl-2,3,4,6-tetraacetyl-β-D-galactopyranoside

o-nitrophenyl D-galactopyranoside

Refernces

• 1、 -. "COMPOUNDS COMPRISING CLEAVABLE LINKER AND USES THEREOF". Page/Page column 182. . Retrieved 2020/09/03.
• 2、 Kumar, Vineet,Talisman, Ian Jamie,Malhotra, Sanjay V.. "Application of halide molten salts as novel reaction media for O-glycosidic bond formation". supporting information; experimental part. p. 3377 - 3381. Retrieved 2010/08/19.