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

Base Information

• Chemical Name: methyl 5-amino-2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)benzoate
• CAS No.: 135790-64-6
• Molecular Formula: C₂₂H₂₇NO₁₂
• Molecular Weight: 497.456
• Mol file: 135790-64-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about methyl 5-amino-2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)benzoate 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: 96.46%

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

Reference yield:

5-nitrosalicylic acid (96-97-9) → methyl 5-amino-2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)benzoate (135790-64-6)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 96.46 percent / H₂ / 10 percent Pd-C / ethyl acetate / 3 h / 760 Torr

With quinoline; sulfuric acid; hydrogen; silver(l) oxide; palladium on activated charcoal; In ethyl acetate; 1: Esterification / 2: Substitution / 3: Catalytic hydrogenation;

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

Reference yield:

methyl 2-hydroxy-5-nitrobenzoate (17302-46-4) → methyl 5-amino-2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)benzoate (135790-64-6)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 96.46 percent / H₂ / 10 percent Pd-C / ethyl acetate / 3 h / 760 Torr

With quinoline; hydrogen; silver(l) oxide; palladium on activated charcoal; In ethyl acetate; 1: Substitution / 2: Catalytic hydrogenation;

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

upstream raw materials:

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

5-nitrosalicylic acid

methyl 2-hydroxy-5-nitrobenzoate

Downstream raw materials:

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