methyl [4,5,7,8-tetra-O-acetyl-2,3-di-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranos]onate

Base Information

• Chemical Name: methyl [4,5,7,8-tetra-O-acetyl-2,3-di-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranos]onate
• CAS No.: 150920-80-2
• Molecular Formula: C₃₁H₃₀N₂O₁₉
• Molecular Weight: 734.581
• Mol file: 150920-80-2.mol

Synonyms:methyl [4,5,7,8-tetra-O-acetyl-2,3-di-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranos]onate

Chemical Property of methyl [4,5,7,8-tetra-O-acetyl-2,3-di-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranos]onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl [4,5,7,8-tetra-O-acetyl-2,3-di-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranos]onate

There total 5 articles about methyl [4,5,7,8-tetra-O-acetyl-2,3-di-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranos]onate 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: 70.0%

4-nitro-benzoyl chloride (122-04-3) + Methyl 4,5,7,8-tetra-O-acetyl-α-D-glycero-D-talo-2-octulopyranosonate (150920-79-9) → methyl [4,5,7,8-tetra-O-acetyl-2,3-di-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranos]onate (150920-80-2)

Guidance literature:

With pyridine; for 60h; Ambient temperature;

DOI:10.1016/0008-6215(93)80005-Y

Reference yield:

methyl-4,5,7,8-tetra-O-acetyl-2,6-anhydro-2,3-dideoxy-D-manno-oct-2-enosonat (85382-90-7) → methyl [4,5,7,8-tetra-O-acetyl-2,3-di-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranos]onate (150920-80-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 3-chloroperbenzoic acid / CH₂Cl₂ / 36 h / Heating

2.1: silicagel / ethyl acetate / 12 h / Heating

2.2: silicagel / 12 h / Heating

2.3: 710 mg / N,N-dimethylaminopyridine / pyridine / 24 h

With silica gel; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; ethyl acetate;

DOI:10.1016/S0008-6215(00)00213-5

Reference yield:

Methyl 3,4,5,7,8-penta-O-acetyl-α-D-glycero-D-talo-2-octulopyranosyl bromide (148083-34-5) → methyl [4,5,7,8-tetra-O-acetyl-2,3-di-O-(4-nitrobenzoyl)-D-glycero-α-D-talo-oct-2-ulopyranos]onate (150920-80-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / Ag triflate / methanol; CH₂Cl₂ / 5 h / Ambient temperature

2: 70 percent / pyridine / 60 h / Ambient temperature

With pyridine; silver trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1016/0008-6215(93)80005-Y

upstream raw materials:

methyl-4,5,7,8-tetra-O-acetyl-2,6-anhydro-2,3-dideoxy-D-manno-oct-2-enosonat

4-nitro-benzoyl chloride

Methyl 4,5,7,8-tetra-O-acetyl-α-D-glycero-D-talo-2-octulopyranosonate

Methyl 3,4,5,7,8-penta-O-acetyl-α-D-glycero-D-talo-2-octulopyranosyl bromide

Downstream raw materials:

Allyl O-onate>-(2->6)-2-acetamido-2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-β-D-glucopyranoside

Methyl <4,5,7,8-tetra-O-acetyl-2,3-O-<(1-exo-methoxy)-4-nitrobenzylidene>-β-D-glycero-D-talo-2-octulopyranos>onate

Methyl <4,5,7,8-tetra-O-acetyl-3-O-(4-nitrobenzoyl)-α-D-glycero-D-talo-2-octulopyranosyl bromide>onate