[2R,3R,4S,5S]-3-((triisopropylsilyl)oxy)-5-(4-methoxy-benzyloxy)-2,4-dimethylheptane-1,7-diol

Base Information

Chemical Name:[2R,3R,4S,5S]-3-((triisopropylsilyl)oxy)-5-(4-methoxy-benzyloxy)-2,4-dimethylheptane-1,7-diol
CAS No.:440103-87-7
Molecular Formula:C₂₆H₄₈O₅Si
Molecular Weight:468.75
Hs Code.:

Synonyms:[2R,3R,4S,5S]-3-((triisopropylsilyl)oxy)-5-(4-methoxy-benzyloxy)-2,4-dimethylheptane-1,7-diol

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Chemical Property of [2R,3R,4S,5S]-3-((triisopropylsilyl)oxy)-5-(4-methoxy-benzyloxy)-2,4-dimethylheptane-1,7-diol

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Technology Process of [2R,3R,4S,5S]-3-((triisopropylsilyl)oxy)-5-(4-methoxy-benzyloxy)-2,4-dimethylheptane-1,7-diol

There total 1 articles about [2R,3R,4S,5S]-3-((triisopropylsilyl)oxy)-5-(4-methoxy-benzyloxy)-2,4-dimethylheptane-1,7-diol 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: 85.0%

: 440103-86-6
[3R,4R,5S,6S]-4-((triisopropylsilyl)oxy)-6-(4-methoxy-benzyloxy)-3,5-dimethylcycloheptene

: 440103-87-7
[2R,3R,4S,5S]-3-((triisopropylsilyl)oxy)-5-(4-methoxy-benzyloxy)-2,4-dimethylheptane-1,7-diol

Guidance literature:: [3R,4R,5S,6S]-4-((triisopropylsilyl)oxy)-6-(4-methoxy-benzyloxy)-3,5-dimethylcycloheptene; With ozone; In ethanol; dichloromethane; at -78 ℃;

With sodium tetrahydroborate; In ethanol; dichloromethane; at 20 ℃; for 3h; Further stages.;
DOI:10.1021/ol025872f

Reference yield: 93.0%

: 440103-87-7
[2R,3R,4S,5S]-3-((triisopropylsilyl)oxy)-5-(4-methoxy-benzyloxy)-2,4-dimethylheptane-1,7-diol

: 440103-88-8
[2R,3R,4S,4(2S,4S)]-3-((triisopropylsilyl)oxy)-4-[2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2-methyl-pentan-1-ol

Guidance literature:: With 4 A molecular sieve; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at -10 ℃; for 2h;
DOI:10.1021/ol025872f

Reference yield:

: 440103-87-7
[2R,3R,4S,5S]-3-((triisopropylsilyl)oxy)-5-(4-methoxy-benzyloxy)-2,4-dimethylheptane-1,7-diol

: 440104-04-1
[1S,1(2S,5S,2'R,5'S,5'(1R)),2S,3R,4R,5E,8R,10R]-benzoic acid 1-[5'-(1-t-butyldimethylsilyloxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-11-(4-methoxy-benzyloxy)-2,4,8,10-tetramethyl-3-triisopropylsilyloxy-undec-5-enyl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: 93 percent / 2,3-dichloro-4,6-dicyano-1,4-benzoquinone; 4 Angstoem molecular sieves / CH₂Cl₂ / 2 h / -10 °C

2.1: triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 20 h / 20 °C

3.1: 6.0 g / diisobutylaluminium hydride / CH₂Cl₂; heptane / 3 h / -78 - 20 °C

4.1: 90 percent / dimethylsulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / 3.5 h / -78 °C

5.1: n-butyl lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: tetrahydrofuran; hexane / 0.5 h

6.1: N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH₂Cl₂ / 2 h / 20 °C

7.1: 673 mg / samarium diiodide / ethanol; tetrahydrofuran / 0.5 h / -78 °C

8.1: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H₂O; CH₂Cl₂ / 1 h / 0 °C

9.1: 90 percent / samarium diiodide / tetrahydrofuran / 0.5 h / 0 °C

10.1: 4-dimethylaminopyridine / CH₂Cl₂

11.1: HCl / tetrahydrofuran / 5 h / 0 °C

12.1: 264 mg / sodium hydride / tetrahydrofuran / 0.33 h / 50 °C

13.1: 96 percent / Pd(OH)2 / ethanol; cyclohexane / 12 h / Heating

14.1: 91 percent / N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

15.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h

15.2: 85 percent / tetrahydrofuran; toluene / -78 - 20 °C

With hydrogenchloride; dmap; n-butyllithium; samarium diiodide; oxalyl dichloride; 4 A molecular sieve; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; tetrapropylammonium perruthennate; In tetrahydrofuran; ethanol; hexane; n-heptane; dichloromethane; cyclohexane; water; toluene; 4.1: Swern oxidation / 9.1: Tishchenko reaction / 15.1: Julia reaction;
DOI:10.1021/ol025872f