Toluene-4-sulfonic acid (1S,2R,7R)-1-butyl-7-{(2R,5R,2'R,5'R)-5'-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-octahydro-[2,2']bifuranyl-5-yl}-2,7-bis-(2-trimethylsilanyl-ethoxymethoxy)-heptyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (1S,2R,7R)-1-butyl-7-{(2R,5R,2'R,5'R)-5'-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-octahydro-[2,2']bifuranyl-5-yl}-2,7-bis-(2-trimethylsilanyl-ethoxymethoxy)-heptyl ester
• CAS No.: 193949-09-6
• Molecular Formula: C₅₆H₁₁₀O₁₂SSi₄
• Molecular Weight: 1119.89

Synonyms:

Chemical Property of Toluene-4-sulfonic acid (1S,2R,7R)-1-butyl-7-{(2R,5R,2'R,5'R)-5'-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-octahydro-[2,2']bifuranyl-5-yl}-2,7-bis-(2-trimethylsilanyl-ethoxymethoxy)-heptyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (1S,2R,7R)-1-butyl-7-{(2R,5R,2'R,5'R)-5'-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-octahydro-[2,2']bifuranyl-5-yl}-2,7-bis-(2-trimethylsilanyl-ethoxymethoxy)-heptyl ester

There total 14 articles about Toluene-4-sulfonic acid (1S,2R,7R)-1-butyl-7-{(2R,5R,2'R,5'R)-5'-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-octahydro-[2,2']bifuranyl-5-yl}-2,7-bis-(2-trimethylsilanyl-ethoxymethoxy)-heptyl 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: 94.0%

p-toluenesulfonyl chloride (98-59-9) + (5S,6R,11R)-11-{(2R,5R,2'R,5'R)-5'-[(R)-6-(tert-Butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-octahydro-[2,2']bifuranyl-5-yl}-6,11-bis-(2-trimethylsilanyl-ethoxymethoxy)-undecan-5-ol (193949-07-4) → Toluene-4-sulfonic acid (1S,2R,7R)-1-butyl-7-{(2R,5R,2'R,5'R)-5'-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-octahydro-[2,2']bifuranyl-5-yl}-2,7-bis-(2-trimethylsilanyl-ethoxymethoxy)-heptyl ester (193949-09-6)

Guidance literature:

With pyridine;

DOI:10.1021/jo970424k

Reference yield:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → Toluene-4-sulfonic acid (1S,2R,7R)-1-butyl-7-{(2R,5R,2'R,5'R)-5'-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-octahydro-[2,2']bifuranyl-5-yl}-2,7-bis-(2-trimethylsilanyl-ethoxymethoxy)-heptyl ester (193949-09-6)

Guidance literature:

Multi-step reaction with 11 steps

2: 75 percent / pyridine / 1.) 0 deg C, 30 min, 2.) room temperature, 18 h

3: 76 percent / TBAF / tetrahydrofuran / 12 h / 50 °C

4: 1.) NaH / 1.) THF, room temperature, 30 min, 2.) 40 min

5: 85 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 - 20 °C

6: 81 percent / InCl₃ / ethyl acetate

7: 94 percent / i-Pr₂NEt

8: 90 percent / H₂ / Rh/Al₂O₃

9: 94 percent / TBAF

10: 84 percent / Et₃N, DMAP

11: 94 percent / pyridine

With pyridine; dmap; indium(III) chloride; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; Rh/Al₂O₃; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/jo970424k

Reference yield:

(2E)-6-((tert-butyldimethylsilyl)oxy)hex-2-enal (163277-83-6) → Toluene-4-sulfonic acid (1S,2R,7R)-1-butyl-7-{(2R,5R,2'R,5'R)-5'-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-octahydro-[2,2']bifuranyl-5-yl}-2,7-bis-(2-trimethylsilanyl-ethoxymethoxy)-heptyl ester (193949-09-6)

Guidance literature:

Multi-step reaction with 11 steps

2: 75 percent / pyridine / 1.) 0 deg C, 30 min, 2.) room temperature, 18 h

3: 76 percent / TBAF / tetrahydrofuran / 12 h / 50 °C

4: 1.) NaH / 1.) THF, room temperature, 30 min, 2.) 40 min

5: 85 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 - 20 °C

6: 81 percent / InCl₃ / ethyl acetate

7: 94 percent / i-Pr₂NEt

8: 90 percent / H₂ / Rh/Al₂O₃

9: 94 percent / TBAF

10: 84 percent / Et₃N, DMAP

11: 94 percent / pyridine

With pyridine; dmap; indium(III) chloride; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; Rh/Al₂O₃; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/jo970424k

upstream raw materials:

p-toluenesulfonyl chloride

(5S,6R,11R)-11-{(2R,5R,2'R,5'R)-5'-[(R)-6-(tert-Butyl-dimethyl-silanyloxy)-1-(2-trimethylsilanyl-ethoxymethoxy)-hexyl]-octahydro-[2,2']bifuranyl-5-yl}-6,11-bis-(2-trimethylsilanyl-ethoxymethoxy)-undecan-5-ol

(2-trimethylethylsilylethoxy)methyl chloride

(2E)-6-((tert-butyldimethylsilyl)oxy)hex-2-enal

Downstream raw materials:

(S)-3-{(R)-13-[(2R,5R,2'R,5'R)-5'-((1R,6S)-1,6-Dihydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-13-hydroxy-tridecyl}-5-methyl-5H-furan-2-one

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