Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-hexadec-10-en-15-ynyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-hexadec-10-en-15-ynyl ester
• CAS No.: 507480-62-8
• Molecular Formula: C₅₀H₉₂O₁₀SSi₂
• Molecular Weight: 941.511

Synonyms:Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-hexadec-10-en-15-ynyl ester

Chemical Property of Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-hexadec-10-en-15-ynyl ester

Chemical Property:

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Technology Process of Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-hexadec-10-en-15-ynyl ester

There total 8 articles about Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-hexadec-10-en-15-ynyl 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: 86.0%

Toluene-4-sulfonic acid (1S,2R)-1-[(3R,4R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-7-oxo-heptyl]-2-methoxymethoxy-dodecyl ester (247200-07-3) + Tributyl-((E)-(R)-1-methoxymethoxy-oct-2-en-7-ynyl)-stannane → Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-hexadec-10-en-15-ynyl ester (507480-62-8) + toluene-4-sulfonic acid 4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-(1-methoxymethoxy-undecyl)-hexadec-10-en-15-ynyl ester

Guidance literature:

With indium(III) bromide; In ethyl acetate; at -78 - 20 ℃;

DOI:10.1021/jo026433x

Reference yield: 74.0%

Toluene-4-sulfonic acid (1S,2R)-1-[(3R,4R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-7-oxo-heptyl]-2-methoxymethoxy-dodecyl ester (247200-07-3) + Tributyl-((E)-(R)-1-methoxymethoxy-oct-2-en-7-ynyl)-stannane → Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-hexadec-10-en-15-ynyl ester (507480-62-8)

Guidance literature:

With indium(III) bromide; In ethyl acetate; at 20 ℃; for 18h;

DOI:10.1021/jo026433x

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (E)-(1S,4R,5R,8S,9R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-9-methoxymethoxy-1-((R)-1-methoxymethoxy-undecyl)-hexadec-10-en-15-ynyl ester (507480-62-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / pyridine

2: H₂ / Pd/C

3: PCC

4: 74 percent / InBr₃ / ethyl acetate / 18 h / 20 °C

With pyridine; indium(III) bromide; hydrogen; pyridinium chlorochromate; palladium on activated charcoal; In ethyl acetate;

DOI:10.1021/jo026433x

upstream raw materials:

Toluene-4-sulfonic acid (1S,2R)-1-[(3R,4R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-7-oxo-heptyl]-2-methoxymethoxy-dodecyl ester

p-toluenesulfonyl chloride

(4R,5R)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-octanal

(E)-(4R,5R,8S,9R)-1-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-nonadec-10-en-8-ol

Downstream raw materials:

(+)-asimicin

C₅₇H₉₈O₁₂S₂Si₂

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