toluene-4-sulfonic acid 3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl ester

Base Information

• Chemical Name: toluene-4-sulfonic acid 3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl ester
• CAS No.: 527743-03-9
• Molecular Formula: C₂₄H₄₀O₅SSi
• Molecular Weight: 468.73
• Mol file: 527743-03-9.mol

Synonyms:toluene-4-sulfonic acid 3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl ester

Chemical Property of toluene-4-sulfonic acid 3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of toluene-4-sulfonic acid 3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl ester

There total 10 articles about toluene-4-sulfonic acid 3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl 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:

p-toluenesulfonyl chloride (98-59-9) + (2R)-3-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methylpropan-1-ol (312695-90-2) → toluene-4-sulfonic acid 3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl ester (527743-03-9)

Guidance literature:

With dmap; TEA; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4039(02)00472-0

Reference yield:

(3R)-4-(4-methoxybenzyloxy)-3-methylbutyraldehyde (259198-97-5) → toluene-4-sulfonic acid 3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl ester (527743-03-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: (-)-methoxydiisopinocampheylborane / diethyl ether / 3 h / 20 °C

1.2: diethyl ether; pentane / 1 h / -100 °C

1.3: 93 percent / NaBO₃*4H₂O / tetrahydrofuran; H₂O / 2 h / 20 °C

2.1: 84 percent / PPTS / toluene / 2 h / 40 °C / 60004.8 Torr

3.1: 94 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 1 h / 40 °C

4.1: montmorillonite K-10 clay / CH₂Cl₂ / 0.5 h / 20 °C

4.2: 86 percent / montmorillonite K₁₀ clay / CH₂Cl₂; H₂O / 1 h / 20 °C

5.1: 99 percent / NaBH₄ / methanol / 0.5 h / 0 °C

6.1: 90 percent / imidazole / CH₂Cl₂; dimethylformamide / 16 h / 20 °C

7.1: 91 percent / DDQ / CH₂Cl₂ / 0.5 h / 20 °C

8.1: Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; Montmorillonite K-10 clay; pyridinium p-toluenesulfonate; triethylamine; (-)-B-methoxydiisopinocampheylborane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Grubbs catalyst first generation; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo026743f

Reference yield:

(4S,6R)-7-(p-methoxybenzyloxy)-6-methylhept-1-en-4-ol (259198-98-6) → toluene-4-sulfonic acid 3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl ester (527743-03-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 84 percent / PPTS / toluene / 2 h / 40 °C / 60004.8 Torr

2.1: 94 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 1 h / 40 °C

3.1: montmorillonite K-10 clay / CH₂Cl₂ / 0.5 h / 20 °C

3.2: 86 percent / montmorillonite K₁₀ clay / CH₂Cl₂; H₂O / 1 h / 20 °C

4.1: 99 percent / NaBH₄ / methanol / 0.5 h / 0 °C

5.1: 90 percent / imidazole / CH₂Cl₂; dimethylformamide / 16 h / 20 °C

6.1: 91 percent / DDQ / CH₂Cl₂ / 0.5 h / 20 °C

7.1: Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; Montmorillonite K-10 clay; pyridinium p-toluenesulfonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Grubbs catalyst first generation; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo026743f

upstream raw materials:

p-toluenesulfonyl chloride

(2R)-3-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methylpropan-1-ol

(3R)-4-(4-methoxybenzyloxy)-3-methylbutyraldehyde

(3R)-4-(4-methoxybenzyloxy)-3-methylbutyrnitrile

Downstream raw materials:

laulimalide

2-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-8-(tert-butyl-diphenyl-silanyloxy)-9-methoxymethoxy-11-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-undeca-1,5,10-trien-4-ol

C₅₄H₈₄O₈Si₂

4-[1-[2-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-allyl]-5-(tert-butyl-diphenyl-silanyloxy)-6-methoxymethoxy-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienyloxy]-pentan-2-ol