methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-nitrobenzoate

Base Information

• Chemical Name: methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-nitrobenzoate
• CAS No.: 135790-63-5
• Molecular Formula: C₂₂H₂₅NO₁₄
• Molecular Weight: 527.439
• Mol file: 135790-63-5.mol

Synonyms:methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-nitrobenzoate

Chemical Property of methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-nitrobenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-nitrobenzoate

There total 2 articles about methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-nitrobenzoate 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: 49.7%

methyl 2-hydroxy-5-nitrobenzoate (17302-46-4) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-nitrobenzoate (135790-63-5)

Guidance literature:

With quinoline; silver(l) oxide; at 20 ℃; for 1h;

DOI:10.1002/(SICI)1521-4184(19999)332:9<321::AID-ARDP321>3.0.CO;2-A

Reference yield:

5-nitrosalicylic acid (96-97-9) → methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-nitrobenzoate (135790-63-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 57.86 percent / conc. H₂SO₄ / 9 h / Heating

2: 49.7 percent / Ag₂O; quinoline / 1 h / 20 °C

With quinoline; sulfuric acid; silver(l) oxide; 1: Esterification / 2: Substitution;

DOI:10.1002/(SICI)1521-4184(19999)332:9<321::AID-ARDP321>3.0.CO;2-A

Reference yield: 96.46%

methyl 2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-nitrobenzoate (135790-63-5) → methyl 5-amino-2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)benzoate (135790-64-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 3h; under 760 Torr;

DOI:10.1002/(SICI)1521-4184(19999)332:9<321::AID-ARDP321>3.0.CO;2-A

upstream raw materials:

methyl 2-hydroxy-5-nitrobenzoate

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

5-nitrosalicylic acid

Downstream raw materials:

methyl 5-amino-2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)benzoate

methyl 2-(β-D-glucopyranosyloxy)-5-aminobenzoate