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
Hs Code.:

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

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

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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

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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-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%

: 98-59-9
p-toluenesulfonyl chloride

: (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

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

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1016/j.bmcl.2006.03.082

Reference yield: 98.0%

: 107-30-2
chloromethyl methyl ether

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

: 596828-45-4
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

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 15h;
DOI:10.1016/j.bmcl.2006.03.082

Reference yield:

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

: 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