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

Base Information

• Chemical Name: benzyl (2,4,5,7,8-penta-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosyl)onate
• CAS No.: 113955-18-3
• Molecular Formula: C₂₅H₃₀O₁₃
• Molecular Weight: 538.505
• Mol file: 113955-18-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about benzyl (2,4,5,7,8-penta-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosyl)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: 78.0%

phenyldiazomethane (908094-04-2) + 2,4,5,7,8-Penta-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosonic acid (73508-80-2) → benzyl (2,4,5,7,8-penta-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosyl)onate (113955-18-3)

Guidance literature:

In dichloromethane; Petroleum ether; for 2h; Ambient temperature;

DOI:10.1248/cpb.35.4537

Reference yield: 73.0%

ammonium 2,4,5,7,8-penta-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosylonate + benzyl bromide (100-39-0) → benzyl (2,4,5,7,8-penta-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosyl)onate (113955-18-3)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.joc.6b01431

Reference yield:

benzyl bromide (100-39-0) + 2,4,5,7,8-Penta-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosonic acid (73508-80-2) → benzyl (2,4,5,7,8-penta-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosyl)onate (113955-18-3)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; caesium carbonate; In N,N-dimethyl-formamide; for 4h; Yield given; Ambient temperature;

DOI:10.1021/ja00055a008

upstream raw materials:

phenyldiazomethane

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

benzyl bromide

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

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

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

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