Toluene-4-sulfonic acid (1S,4R,5R)-1-[(E)-(1R,4R)-4,11-bis-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-undec-2-enyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-nonadecyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (1S,4R,5R)-1-[(E)-(1R,4R)-4,11-bis-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-undec-2-enyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-nonadecyl ester
• CAS No.: 204976-83-0
• Molecular Formula: C₅₉H₁₁₆O₁₀SSi₃
• Molecular Weight: 1101.89

Synonyms:

Chemical Property of Toluene-4-sulfonic acid (1S,4R,5R)-1-[(E)-(1R,4R)-4,11-bis-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-undec-2-enyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-nonadecyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (1S,4R,5R)-1-[(E)-(1R,4R)-4,11-bis-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-undec-2-enyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-nonadecyl ester

There total 6 articles about Toluene-4-sulfonic acid (1S,4R,5R)-1-[(E)-(1R,4R)-4,11-bis-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-undec-2-enyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-nonadecyl 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: 96.0%

p-toluenesulfonyl chloride (98-59-9) + (E)-(8R,11R,12S,15R,16R)-1,8,15-Tris-(tert-butyl-dimethyl-silanyloxy)-11,16-bis-methoxymethoxy-triacont-9-en-12-ol (204976-82-9) → Toluene-4-sulfonic acid (1S,4R,5R)-1-[(E)-(1R,4R)-4,11-bis-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-undec-2-enyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-nonadecyl ester (204976-83-0)

Guidance literature:

With pyridine;

DOI:10.1016/S0040-4039(98)00007-0

Reference yield:

Tributyl-[(S)-1-((Z)-2-methoxymethoxy-vinyl)-tridecyl]-stannane → Toluene-4-sulfonic acid (1S,4R,5R)-1-[(E)-(1R,4R)-4,11-bis-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-undec-2-enyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-nonadecyl ester (204976-83-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

2: 93 percent / imidazole

3: 100 percent / H₂ / Rh-Al₂O₃

4: 87 percent / i-Bu₂AlH / hexane

5: 72 percent / InBr₃ / diethyl ether / -30 °C

6: 96 percent / pyridine

With pyridine; 1H-imidazole; indium(III) bromide; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; rhodium on alumina; In diethyl ether; hexane; dichloromethane;

DOI:10.1016/S0040-4039(98)00007-0

Reference yield:

(2E,6E)-(4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methoxymethoxy-nonadeca-2,6-dienoic acid ethyl ester (204976-79-4) → Toluene-4-sulfonic acid (1S,4R,5R)-1-[(E)-(1R,4R)-4,11-bis-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-undec-2-enyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxymethoxy-nonadecyl ester (204976-83-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / H₂ / Rh-Al₂O₃

2: 87 percent / i-Bu₂AlH / hexane

3: 72 percent / InBr₃ / diethyl ether / -30 °C

4: 96 percent / pyridine

With pyridine; indium(III) bromide; hydrogen; diisobutylaluminium hydride; rhodium on alumina; In diethyl ether; hexane;

DOI:10.1016/S0040-4039(98)00007-0

upstream raw materials:

p-toluenesulfonyl chloride

(E)-(8R,11R,12S,15R,16R)-1,8,15-Tris-(tert-butyl-dimethyl-silanyloxy)-11,16-bis-methoxymethoxy-triacont-9-en-12-ol

(4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methoxymethoxy-nonadecanal

(4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methoxymethoxy-nonadecanoic acid ethyl ester

Downstream raw materials:

Longifolicin

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