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

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-hydroxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester
• CAS No.: 900865-45-4
• Molecular Formula: C₃₁H₅₆O₈SSi₂
• Molecular Weight: 645.018
• Mol file: 900865-45-4.mol

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-hydroxy-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-hydroxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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-hydroxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester

There total 1 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-hydroxy-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: 55.0%

p-toluenesulfonyl chloride (98-59-9) + (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-hydroxy-ethyl]-octahydro-[2,2']bifuranyl-5-yl}-ethyl ester (900865-45-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/j.bmcl.2006.03.082

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:

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) → Q-acetogenin

Guidance literature:

Multi-step reaction with 12 steps

1: 97 percent / (i-Pr)2NEt

2: 88 percent / TBAF / tetrahydrofuran / 20 °C

3: 69 percent / n-BuLi; BF₃*Et₂O / tetrahydrofuran / 0.5 h / -78 °C

4: 96 percent / DMAP / CH₂Cl₂ / 0 - 20 °C

5: 94 percent / BF₃*Et₂O; Me₂S / 1.5 h / -20 °C

6: 95 percent / DMAP; Et₃N / CH₂Cl₂ / 3 h / 55 °C

7: 92 percent / KOH / methanol / 0.5 h / 20 °C

8: BF₃*Et₂O / 0.25 h / -78 °C

9: K₂CO₃ / methanol / 5 h / 20 °C

10: 72 percent / (Ph₃P)4Pd; CuI; Et₃N / 5 h / 20 °C

11: 91 percent / H₂ / (Ph₃P)3RhCl / benzene / 24 h / 20 °C

12: 86 percent / aq. Ce(NH₄)2(NO₃)6; pyridine-2,6-dicarboxylic acid / acetonitrile / 4 h / 0 °C

With dmap; potassium hydroxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; Pyridine-2,6-dicarboxylic acid; ammonium cerium(IV) nitrate; dimethylsulfide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; Wilkinson's catalyst; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; benzene;

DOI:10.1016/S0960-894X(03)00439-6

upstream raw materials:

p-toluenesulfonyl chloride

Downstream raw materials:

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

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

(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

(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