cyclohexyl 3-O-benzyl-4,6-O-benzylidene-2-O-(4-methoxybenzyl)-β-D-mannopyranoside

Base Information

• Chemical Name: cyclohexyl 3-O-benzyl-4,6-O-benzylidene-2-O-(4-methoxybenzyl)-β-D-mannopyranoside
• CAS No.: 351060-32-7
• Molecular Formula: C₃₄H₄₀O₇
• Molecular Weight: 560.687
• Mol file: 351060-32-7.mol

Synonyms:cyclohexyl 3-O-benzyl-4,6-O-benzylidene-2-O-(4-methoxybenzyl)-β-D-mannopyranoside

Chemical Property of cyclohexyl 3-O-benzyl-4,6-O-benzylidene-2-O-(4-methoxybenzyl)-β-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cyclohexyl 3-O-benzyl-4,6-O-benzylidene-2-O-(4-methoxybenzyl)-β-D-mannopyranoside

There total 4 articles about cyclohexyl 3-O-benzyl-4,6-O-benzylidene-2-O-(4-methoxybenzyl)-β-D-mannopyranoside 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%

cyclohexanol (108-93-0) + ethyl 3-O-benzyl-4,6-O-benzylidene-2-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside S-oxide (808741-03-9) → cyclohexyl 3-O-benzyl-4,6-O-benzylidene-2-O-(4-methoxybenzyl)-β-D-mannopyranoside (351060-32-7)

Guidance literature:

ethyl 3-O-benzyl-4,6-O-benzylidene-2-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside S-oxide; With trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -78 ℃;

cyclohexanol; In dichloromethane; Further stages.;

DOI:10.1021/ja015985e

Reference yield:

ethyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (173935-67-6) → cyclohexyl 3-O-benzyl-4,6-O-benzylidene-2-O-(4-methoxybenzyl)-β-D-mannopyranoside (351060-32-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH; Bu₄NI / dimethylformamide / 0.33 h / 0 °C

1.2: 75 percent / dimethylformamide / 0 - 20 °C

2.1: 84 percent / m-CPBA / CH₂Cl₂ / -78 - -20 °C

3.1: 2,4,6-tri-tert-butylpyrimidine; molecular sieves / CH₂Cl₂ / 0.17 h / -78 °C

4.1: 1.20 g / CH₂Cl₂ / -78 - -30 °C

With molecular sieve; tetra-(n-butyl)ammonium iodide; sodium hydride; 3-chloro-benzenecarboperoxoic acid; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja047194t

Reference yield:

ethyl 3-O-benzyl-4,6-O-benzylidene-2-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside S-oxide (808741-03-9) → cyclohexyl 3-O-benzyl-4,6-O-benzylidene-2-O-(4-methoxybenzyl)-β-D-mannopyranoside (351060-32-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,4,6-tri-tert-butylpyrimidine; molecular sieves / CH₂Cl₂ / 0.17 h / -78 °C

2: 1.20 g / CH₂Cl₂ / -78 - -30 °C

With molecular sieve; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane;

DOI:10.1021/ja047194t

upstream raw materials:

cyclohexanol

ethyl 3-O-benzyl-4,6-O-benzylidene-2-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside S-oxide

ethyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Downstream raw materials:

cyclohexyl 3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside

cyclohexyl 3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->2)-3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside

cyclohexyl 3-O-benzyl-4,6-O-benzylidene-2-O-(4-methoxybenzyl)-β-D-mannopyranosyl-(1->2)-3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside

cyclohexyl 3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->2)-3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->2)-3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside