Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-{(2R,5R,2'R,5'R)-5'-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-{(2R,5R,2'R,5'R)-5'-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester
• CAS No.: 596828-45-4
• Molecular Formula: C₃₃H₆₀O₉SSi₂
• Molecular Weight: 689.071

Synonyms:Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-{(2R,5R,2'R,5'R)-5'-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester

Chemical Property of Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-{(2R,5R,2'R,5'R)-5'-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester

Chemical Property:

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Technology Process of Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-{(2R,5R,2'R,5'R)-5'-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester

There total 4 articles about Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-{(2R,5R,2'R,5'R)-5'-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl 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: 98.0%

chloromethyl methyl ether (107-30-2) + Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-{(2R,5R,2'R,5'R)-5'-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester (900865-45-4) → Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-{(2R,5R,2'R,5'R)-5'-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester (596828-45-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1016/j.bmcl.2006.03.082

Reference yield:

(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,5R,2'R,5'R)-5'-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethanol → Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-{(2R,5R,2'R,5'R)-5'-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester (596828-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / 4-DMAP; Et₃N / CH₂Cl₂ / 24 h / 20 °C

2: 98 percent / i-Pr₂NEt / CH₂Cl₂ / 15 h / 20 °C

With dmap; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/j.bmcl.2006.03.082

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-{(2R,5R,2'R,5'R)-5'-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester (596828-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / 4-DMAP; Et₃N / CH₂Cl₂ / 24 h / 20 °C

2: 98 percent / i-Pr₂NEt / CH₂Cl₂ / 15 h / 20 °C

With dmap; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/j.bmcl.2006.03.082

upstream raw materials:

chloromethyl methyl ether

Toluene-4-sulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-{(2R,5R,2'R,5'R)-5'-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester

p-toluenesulfonyl chloride

Downstream raw materials:

(R)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-Hydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-13-(2,3,4,5-tetramethoxy-6-methyl-phenyl)-tridecan-1-ol

(E)-(R)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-Hydroxy-undec-3-ynyl)-octahydro-[2,2']bifuranyl-5-yl]-13-(2,3,4,5-tetramethoxy-6-methyl-phenyl)-tridec-5-en-3-yn-1-ol

Acetic acid (S)-2-[(2R,5R,2'R,5'R)-5'-((R)-1-acetoxy-undec-3-ynyl)-octahydro-[2,2']bifuranyl-5-yl]-2-(toluene-4-sulfonyloxy)-ethyl ester

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