Methanesulfonic acid 5-benzyloxy-2-[5-(tert-butyldiphenylsilanyloxy)-1-hydroxy-3-methoxy-4-methylpentyl]pent-3-enyl ester

Base Information

• Chemical Name: Methanesulfonic acid 5-benzyloxy-2-[5-(tert-butyldiphenylsilanyloxy)-1-hydroxy-3-methoxy-4-methylpentyl]pent-3-enyl ester
• CAS No.: 301230-13-7
• Molecular Formula: C₃₆H₅₀O₇SSi
• Molecular Weight: 654.94
• Mol file: 301230-13-7.mol

Synonyms:Methanesulfonic acid 5-benzyloxy-2-[5-(tert-butyldiphenylsilanyloxy)-1-hydroxy-3-methoxy-4-methylpentyl]pent-3-enyl ester

Chemical Property of Methanesulfonic acid 5-benzyloxy-2-[5-(tert-butyldiphenylsilanyloxy)-1-hydroxy-3-methoxy-4-methylpentyl]pent-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid 5-benzyloxy-2-[5-(tert-butyldiphenylsilanyloxy)-1-hydroxy-3-methoxy-4-methylpentyl]pent-3-enyl ester

There total 15 articles about Methanesulfonic acid 5-benzyloxy-2-[5-(tert-butyldiphenylsilanyloxy)-1-hydroxy-3-methoxy-4-methylpentyl]pent-3-enyl ester 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: 90.0%

methanesulfonyl chloride (124-63-0) + 2-(3-Benzyloxyprop-1-enyl)-7-(tert-butyldiphenylsilanyloxy)-5-methoxy-6-methylheptane-1,3-diol (301230-12-6) → Methanesulfonic acid 5-benzyloxy-2-[5-(tert-butyldiphenylsilanyloxy)-1-hydroxy-3-methoxy-4-methylpentyl]pent-3-enyl ester (301230-13-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1039/b000751j

Reference yield:

ethyl (2E)-5-(benzyloxy)pent-2-enoate (70542-83-5) → Methanesulfonic acid 5-benzyloxy-2-[5-(tert-butyldiphenylsilanyloxy)-1-hydroxy-3-methoxy-4-methylpentyl]pent-3-enyl ester (301230-13-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 84 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / 0 °C

2.1: Ti(O-i-Pr)4; (-)-diethyl tartrate; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / -20 °C

2.2: 61 percent / t-BuOOH / CH₂Cl₂; 2,2,4-trimethyl-pentane / -20 °C

3.1: CuI / tetrahydrofuran / 0.5 h / -20 °C

3.2: 66 percent / tetrahydrofuran / 2.5 h / -20 °C

4.1: 94 percent / imidazole / dimethylformamide / 20 °C

5.1: NaH / dimethylformamide / 0.08 h / 0 °C

5.2: 66 percent / dimethylformamide / 2 h / 20 °C

6.1: 92 percent / H₂ / Pearlman's catalyst / methanol / 18 h

7.1: 87 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

8.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

8.2: 70 percent / CH₂Cl₂ / 3.5 h / -78 - 0 °C

9.1: 90 percent / LiBH₄ / tetrahydrofuran; methanol / 0.5 h / 0 °C

10.1: 90 percent / (i-Pr)2NEt / CH₂Cl₂ / 2 h / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; copper(l) iodide; lithium borohydride; oxalyl dichloride; 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Substitution / 2.2: Epoxidation / 3.1: Transmetallation / 3.2: Methylation / 4.1: Substitution / 5.1: Metallation / 5.2: Methylation / 6.1: Hydrogenolysis / 7.1: Oxidation / 8.1: Addition / 8.2: Condensation / 9.1: Reduction / 10.1: Substitution;

DOI:10.1039/b000751j

Reference yield:

[3-(2-Benzyloxyethyl)oxiran-2-yl]methanol (89956-14-9) → Methanesulfonic acid 5-benzyloxy-2-[5-(tert-butyldiphenylsilanyloxy)-1-hydroxy-3-methoxy-4-methylpentyl]pent-3-enyl ester (301230-13-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: CuI / tetrahydrofuran / 0.5 h / -20 °C

1.2: 66 percent / tetrahydrofuran / 2.5 h / -20 °C

2.1: 94 percent / imidazole / dimethylformamide / 20 °C

3.1: NaH / dimethylformamide / 0.08 h / 0 °C

3.2: 66 percent / dimethylformamide / 2 h / 20 °C

4.1: 92 percent / H₂ / Pearlman's catalyst / methanol / 18 h

5.1: 87 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

6.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

6.2: 70 percent / CH₂Cl₂ / 3.5 h / -78 - 0 °C

7.1: 90 percent / LiBH₄ / tetrahydrofuran; methanol / 0.5 h / 0 °C

8.1: 90 percent / (i-Pr)2NEt / CH₂Cl₂ / 2 h / 0 - 20 °C

With 1H-imidazole; copper(l) iodide; lithium borohydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Transmetallation / 1.2: Methylation / 2.1: Substitution / 3.1: Metallation / 3.2: Methylation / 4.1: Hydrogenolysis / 5.1: Oxidation / 6.1: Addition / 6.2: Condensation / 7.1: Reduction / 8.1: Substitution;

DOI:10.1039/b000751j

upstream raw materials:

methanesulfonyl chloride

2-(3-Benzyloxyprop-1-enyl)-7-(tert-butyldiphenylsilanyloxy)-5-methoxy-6-methylheptane-1,3-diol

3-benzyloxypropan-1-ol

ethyl (2E)-5-(benzyloxy)pent-2-enoate

Downstream raw materials:

1-Benzyloxy-9-(tert-butyldiphenylsilanyloxy)-7-methoxy-4,8-dimethylnon-2-en-5-ol

1-(tert-Butyldiphenylsilanyloxy)-3,7-dimethoxy-2,6-dimethyldec-9-en-5-ol

tert-Butyl(3,7-dimethoxy-5-methoxomethoxy-2,6-dimethyldec-9-enyloxy)diphenylsilane

3-(tert-Butyldimethylsilanyloxy)-7-(tert-butyldiphenylsilanyloxy)-5-methoxy-2,6-dimethylheptanal