Toluene-4-sulfonic acid (R)-2-[(S)-1-((1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-octahydro-inden-1-yl)-ethyl]-5-methyl-5-triethylsilanyloxy-hexyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (R)-2-[(S)-1-((1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-octahydro-inden-1-yl)-ethyl]-5-methyl-5-triethylsilanyloxy-hexyl ester
• CAS No.: 386743-53-9
• Molecular Formula: C₃₂H₅₆O₅SSi
• Molecular Weight: 580.945
• Mol file: 386743-53-9.mol

Synonyms:Toluene-4-sulfonic acid (R)-2-[(S)-1-((1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-octahydro-inden-1-yl)-ethyl]-5-methyl-5-triethylsilanyloxy-hexyl ester

Chemical Property of Toluene-4-sulfonic acid (R)-2-[(S)-1-((1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-octahydro-inden-1-yl)-ethyl]-5-methyl-5-triethylsilanyloxy-hexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (R)-2-[(S)-1-((1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-octahydro-inden-1-yl)-ethyl]-5-methyl-5-triethylsilanyloxy-hexyl ester

There total 5 articles about Toluene-4-sulfonic acid (R)-2-[(S)-1-((1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-octahydro-inden-1-yl)-ethyl]-5-methyl-5-triethylsilanyloxy-hexyl 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: 76.0%

p-toluenesulfonyl chloride (98-59-9) + (1R,3aR,4S,7aR)-1-((1S,2R)-2-Hydroxymethyl-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-7a-methyl-octahydro-inden-4-ol (308123-42-4) → Toluene-4-sulfonic acid (R)-2-[(S)-1-((1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-octahydro-inden-1-yl)-ethyl]-5-methyl-5-triethylsilanyloxy-hexyl ester (386743-53-9)

Guidance literature:

With pyridine; at 0 ℃; for 12h;

DOI:10.1055/s-2001-17446

Reference yield:

2-[(S)-1-((1R,3aR,4S,7aR)-4-Hydroxy-7a-methyl-octahydro-inden-1-yl)-ethyl]-5-methyl-5-triethylsilanyloxy-hexanenitrile (145223-32-1) → Toluene-4-sulfonic acid (R)-2-[(S)-1-((1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-octahydro-inden-1-yl)-ethyl]-5-methyl-5-triethylsilanyloxy-hexyl ester (386743-53-9)

Guidance literature:

Multi-step reaction with 3 steps

1: DIBAH / CH₂Cl₂ / -10 °C

2: NaBH₄ / methanol

3: 76 percent / pyridine / 12 h / 0 °C

With pyridine; sodium tetrahydroborate; diisobutylaluminium hydride; In methanol; dichloromethane;

DOI:10.1055/s-2001-17446

Reference yield:

<1R-<1β(R*),3aα,4β,7aβ>>-octahydro-4-hydroxy-β,7a-dimethyl-1H-indene-1-propanenitrile (93489-60-2) → Toluene-4-sulfonic acid (R)-2-[(S)-1-((1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-octahydro-inden-1-yl)-ethyl]-5-methyl-5-triethylsilanyloxy-hexyl ester (386743-53-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran / -78 °C

1.2: 89 percent / tetrahydrofuran / -78 - 20 °C

2.1: DIBAH / CH₂Cl₂ / -10 °C

3.1: NaBH₄ / methanol

4.1: 76 percent / pyridine / 12 h / 0 °C

With pyridine; sodium tetrahydroborate; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1055/s-2001-17446

upstream raw materials:

p-toluenesulfonyl chloride

(1R,3aR,4S,7aR)-1-((1S,2R)-2-Hydroxymethyl-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-7a-methyl-octahydro-inden-4-ol

<1R-<1β(R*),3aα,4β,7aβ>>-octahydro-4-hydroxy-β,7a-dimethyl-1H-indene-1-propanenitrile

(3-bromo-1,1-dimethylpropoxy)triethylsilane