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

Base Information

• Chemical Name: 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
• CAS No.: 106044-09-1
• Molecular Formula: C₄₈H₅₄NO₁₉P
• Molecular Weight: 979.926
• Mol file: 106044-09-1.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 7 articles about 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 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: 79.0%

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) → 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 (106044-09-1)

Guidance literature:

With zinc; In acetic acid; for 6h; Ambient temperature;

DOI:10.1248/cpb.35.4537

Reference yield:

benzyl 4,5,7,8-tetra-O-acetyl-2-bromo-3-deoxy-α-D-manno-2-octulosonate (106022-64-4) → 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 (106044-09-1)

Guidance literature:

Multi-step reaction with 3 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.

3: 79 percent / zinc / acetic acid / 6 h / Ambient temperature

With dmap; 4 A molecular sieve; mercury(II) cyanide; mercury dibromide; zinc; In acetic acid;

DOI:10.1248/cpb.35.4537

Reference yield:

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) → 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 (106044-09-1)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 79 percent / zinc / acetic acid / 6 h / Ambient temperature

With dmap; 4 A molecular sieve; zinc; In acetic acid;

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-4-O-diphenylphosphono-2-(2,2,2-trichloroethoxycarbonyl)amino-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside

phenyldiazomethane

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

benzyl (2,4,5,7,8-penta-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosyl)onate

Downstream raw materials:

benzyl 6-O-(benzyl 4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylonate)-2-deoxy-4-O-diphenylphosphono-2-<(R)-3-tetradecanoyloxytetradecanamido>-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranoside