[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(4-nitrophenoxy)oxan-2-yl]methyl acetate

Base Information

• Chemical Name: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(4-nitrophenoxy)oxan-2-yl]methyl acetate
• CAS No.: 17042-39-6
• Molecular Formula: C20H23 N O12
• Molecular Weight: 469.402
• Hs Code.: 2938909090
• Mol file: 17042-39-6.mol

Synonyms:17042-39-6;[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(4-nitrophenoxy)oxan-2-yl]methyl acetate;alpha-D-Galactopyranoside, 4-nitrophenyl, 2,3,4,6-tetraacetate;p-Nitrophenyl 2,3,4,6-Tetra-O-acetyl-alpha-D-galactopyranoside;(2R,3S,4S,5R,6R)-2-(Acetoxymethyl)-6-(4-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate;(4-NITRO)PHENYL-2,3,4,6-TETRA-O-ACETYL-alpha-D-GALACTOPYRANOSIDE;NSC 89590;4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside;p-Nitrophenyl 2,3,4,6-Tetra-O-acetyl-?-D-galactopyranoside;p-Nitrophenyl 2,3,4,6-Tetra-O-acetyl- alpha -D-galactopyranoside;(2R,3S,4S,5R,6R)-2-(Acetoxymethyl)-6-(4-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyltriacetate

Chemical Property of [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(4-nitrophenoxy)oxan-2-yl]methyl acetate

Chemical Property:

• Vapor Pressure: 1.53E-12mmHg at 25°C
• Melting Point: 129-130 °C
• Boiling Point: 559.3°Cat760mmHg
• Flash Point: 207.1°C
• PSA: 169.48000
• Density: 1.38g/cm³
• LogP: 1.57990
• Solubility.: Chloroform
• 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-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=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-galactopyranoside (cas# 17042-39-6) is a compound useful in organic synthesis.

Technology Process of [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(4-nitrophenoxy)oxan-2-yl]methyl acetate

There total 26 articles about [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(4-nitrophenoxy)oxan-2-yl]methyl acetate 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: 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

Reference yield: 90.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate (86520-63-0) → 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:

4-nitro-phenol; 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate; In dichloromethane; at -25 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With boron trifluoride diethyl etherate; In dichloromethane; for 0.5h; Inert atmosphere;

upstream raw materials:

4-nitro-phenol

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

β-D-galactose peracetate

acetic anhydride

Downstream raw materials:

4-nitrophenyl-β-D-galactopyranoside

4-nitrophenyl α-D-galactoside

Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acetylamino-phenoxy)-tetrahydro-pyran-3-yl ester

5-(-N-(p-O-(2,3,4,6-tetra-O-acetyl-β-D-galactosyl)phenyl)-aminocarbonyl)-2,2'-bipyridine

Refernces

• 1、 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.
• 2、 Nishihara, Tatsuya,Kuno, Satoshi,Nonaka, Hiroshi,Tabata, Sho,Saito, Natsumi,Fukuda, Shinji,Tomita, Masaru,Sando, Shinsuke,Soga, Tomoyoshi. "Beta-galactosidase-responsive synthetic biomarker for targeted tumor detection". supporting information. p. 11745 - 11748. Retrieved 2018/11/25.