benzyl 6-O-(benzyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-deoxy-4-O-diphenylphosphono-2-(2,2,2-trichloroethoxycarbonyl)amino-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside

Base Information

• Chemical Name: benzyl 6-O-(benzyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-deoxy-4-O-diphenylphosphono-2-(2,2,2-trichloroethoxycarbonyl)amino-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside
• CAS No.: 106022-77-9
• Molecular Formula: C₅₄H₅₆Cl₆NO₂₃P
• Molecular Weight: 1330.72
• Mol file: 106022-77-9.mol

Synonyms:benzyl 6-O-(benzyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-deoxy-4-O-diphenylphosphono-2-(2,2,2-trichloroethoxycarbonyl)amino-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside

Chemical Property of benzyl 6-O-(benzyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-deoxy-4-O-diphenylphosphono-2-(2,2,2-trichloroethoxycarbonyl)amino-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 6-O-(benzyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-deoxy-4-O-diphenylphosphono-2-(2,2,2-trichloroethoxycarbonyl)amino-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside

There total 6 articles about benzyl 6-O-(benzyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-deoxy-4-O-diphenylphosphono-2-(2,2,2-trichloroethoxycarbonyl)amino-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside 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: 77.0%

benzyl 6-O-(benzyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-deoxy-2-(2,2,2-trichloroethoxycarbonyl)amino-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside (106022-75-7) + chlorophosphoric acid diphenyl ester (2524-64-3) → benzyl 6-O-(benzyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-deoxy-4-O-diphenylphosphono-2-(2,2,2-trichloroethoxycarbonyl)amino-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside (106022-77-9)

Guidance literature:

With pyridine; dmap; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1248/cpb.34.2302

Reference yield:

benzyl 4,5,7,8-tetra-O-acetyl-2-bromo-3-deoxy-α-D-manno-2-octulosonate (106022-64-4) → benzyl 6-O-(benzyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-deoxy-4-O-diphenylphosphono-2-(2,2,2-trichloroethoxycarbonyl)amino-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside (106022-77-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Hg(CN)2, HgBr₂, Molecular Sieves 4A / 1.) dichloromethane, 1 h, r.t; 2.) dichloromethane, 20 h, r.t.

2: 1.) 4-dimethylaminopyridine, Molecular Sieves 4A / 1.) pyridine, benzene, 5 degC, 20 min; 2.) pyridine, benzene, 4 h, r.t.

With dmap; 4 A molecular sieve; mercury(II) cyanide; mercury dibromide;

DOI:10.1248/cpb.35.4537

Reference yield:

phenyldiazomethane (908094-04-2) → benzyl 6-O-(benzyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-deoxy-4-O-diphenylphosphono-2-(2,2,2-trichloroethoxycarbonyl)amino-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside (106022-77-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / CH₂Cl₂; petroleum ether / 2 h / Ambient temperature

2: 1.) Molecular Sieves 4A; 2.) titanium tetrabromide / 1.) dichloromethane, ethyl acetate, 60 min, r.t; 2.) dichloromethane, ethyl acetate, 16 h, r.t.

3: 1.) Hg(CN)2, HgBr₂, Molecular Sieves 4A / 1.) dichloromethane, 1 h, r.t; 2.) dichloromethane, 20 h, r.t.

4: 1.) 4-dimethylaminopyridine, Molecular Sieves 4A / 1.) pyridine, benzene, 5 degC, 20 min; 2.) pyridine, benzene, 4 h, r.t.

With dmap; 4 A molecular sieve; mercury(II) cyanide; titanium(IV) bromide; mercury dibromide; In dichloromethane; Petroleum ether;

DOI:10.1248/cpb.35.4537

upstream raw materials:

benzyl 6-O-(benzyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-deoxy-2-(2,2,2-trichloroethoxycarbonyl)amino-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside

chlorophosphoric acid diphenyl ester

phenyldiazomethane

2,4,5,7,8-Penta-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosonic acid

Downstream raw materials:

benzyl 2-amino-6-O-(benzyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-deoxy-4-O-diphenylphosphono-β-D-glucopyranoside