Acetic acid (2E,6E)-(1R,4R,5S,11R)-13-hydroxy-1-[(E)-(1R,2R)-1-(4-methoxy-benzyloxy)-2-methyl-hept-3-enyl]-4,11-dimethyl-10-methylene-5-(2-trimethylsilanyl-ethoxymethoxy)-trideca-2,6-dienyl ester

Base Information

• Chemical Name: Acetic acid (2E,6E)-(1R,4R,5S,11R)-13-hydroxy-1-[(E)-(1R,2R)-1-(4-methoxy-benzyloxy)-2-methyl-hept-3-enyl]-4,11-dimethyl-10-methylene-5-(2-trimethylsilanyl-ethoxymethoxy)-trideca-2,6-dienyl ester
• CAS No.: 216494-48-3
• Molecular Formula: C₄₀H₆₆O₇Si
• Molecular Weight: 687.045
• Mol file: 216494-48-3.mol

Synonyms:Acetic acid (2E,6E)-(1R,4R,5S,11R)-13-hydroxy-1-[(E)-(1R,2R)-1-(4-methoxy-benzyloxy)-2-methyl-hept-3-enyl]-4,11-dimethyl-10-methylene-5-(2-trimethylsilanyl-ethoxymethoxy)-trideca-2,6-dienyl ester

Chemical Property of Acetic acid (2E,6E)-(1R,4R,5S,11R)-13-hydroxy-1-[(E)-(1R,2R)-1-(4-methoxy-benzyloxy)-2-methyl-hept-3-enyl]-4,11-dimethyl-10-methylene-5-(2-trimethylsilanyl-ethoxymethoxy)-trideca-2,6-dienyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2E,6E)-(1R,4R,5S,11R)-13-hydroxy-1-[(E)-(1R,2R)-1-(4-methoxy-benzyloxy)-2-methyl-hept-3-enyl]-4,11-dimethyl-10-methylene-5-(2-trimethylsilanyl-ethoxymethoxy)-trideca-2,6-dienyl ester

There total 17 articles about Acetic acid (2E,6E)-(1R,4R,5S,11R)-13-hydroxy-1-[(E)-(1R,2R)-1-(4-methoxy-benzyloxy)-2-methyl-hept-3-enyl]-4,11-dimethyl-10-methylene-5-(2-trimethylsilanyl-ethoxymethoxy)-trideca-2,6-dienyl 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: 97.0%

Acetic acid (2E,6E)-(1R,4R,5S,11R)-1-[(E)-(1R,2R)-1-(4-methoxy-benzyloxy)-2-methyl-hept-3-enyl]-4,11-dimethyl-10-methylene-13-(tetrahydro-pyran-2-yloxy)-5-(2-trimethylsilanyl-ethoxymethoxy)-trideca-2,6-dienyl ester (216494-47-2) → Acetic acid (2E,6E)-(1R,4R,5S,11R)-13-hydroxy-1-[(E)-(1R,2R)-1-(4-methoxy-benzyloxy)-2-methyl-hept-3-enyl]-4,11-dimethyl-10-methylene-5-(2-trimethylsilanyl-ethoxymethoxy)-trideca-2,6-dienyl ester (216494-48-3)

Guidance literature:

With acetic acid;

DOI:10.1021/ja982572d

Reference yield:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → Acetic acid (2E,6E)-(1R,4R,5S,11R)-13-hydroxy-1-[(E)-(1R,2R)-1-(4-methoxy-benzyloxy)-2-methyl-hept-3-enyl]-4,11-dimethyl-10-methylene-5-(2-trimethylsilanyl-ethoxymethoxy)-trideca-2,6-dienyl ester (216494-48-3)

Guidance literature:

Multi-step reaction with 9 steps

1: iPr₂NEt, DMAP / CH₂Cl₂

2: 1.) Cp₂ZrHCl, 2.) NIS / 1.) CH₂Cl₂, 2.) CH₂Cl₂

3: 84 percent / (PPh₃)4Pd / 22 °C

4: TBAF / tetrahydrofuran

5: Dess-Martin periodinane, NaHCO₃ / CH₂Cl₂

6: CrCl₂ / tetrahydrofuran / Ambient temperature

7: 1.) t-BuLi, 2.) Me₂Zn

8: 94 percent / pyridine, DMAP

9: 97 percent / aq. 80percent AcOH

With pyridine; chromium dichloride; dmap; N-iodo-succinimide; Schwartz's reagent; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; dimethyl zinc(II); tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja982572d

Reference yield:

((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol (127665-69-4) → Acetic acid (2E,6E)-(1R,4R,5S,11R)-13-hydroxy-1-[(E)-(1R,2R)-1-(4-methoxy-benzyloxy)-2-methyl-hept-3-enyl]-4,11-dimethyl-10-methylene-5-(2-trimethylsilanyl-ethoxymethoxy)-trideca-2,6-dienyl ester (216494-48-3)

Guidance literature:

Multi-step reaction with 11 steps

1: NCS, Ph₃P / CH₂Cl₂ / Heating

2: LDA / tetrahydrofuran / -30 °C

3: iPr₂NEt, DMAP / CH₂Cl₂

4: 1.) Cp₂ZrHCl, 2.) NIS / 1.) CH₂Cl₂, 2.) CH₂Cl₂

5: 84 percent / (PPh₃)4Pd / 22 °C

6: TBAF / tetrahydrofuran

7: Dess-Martin periodinane, NaHCO₃ / CH₂Cl₂

8: CrCl₂ / tetrahydrofuran / Ambient temperature

9: 1.) t-BuLi, 2.) Me₂Zn

10: 94 percent / pyridine, DMAP

11: 97 percent / aq. 80percent AcOH

With pyridine; chromium dichloride; dmap; N-chloro-succinimide; N-iodo-succinimide; Schwartz's reagent; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; dimethyl zinc(II); tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja982572d

upstream raw materials:

Acetic acid (2E,6E)-(1R,4R,5S,11R)-1-[(E)-(1R,2R)-1-(4-methoxy-benzyloxy)-2-methyl-hept-3-enyl]-4,11-dimethyl-10-methylene-13-(tetrahydro-pyran-2-yloxy)-5-(2-trimethylsilanyl-ethoxymethoxy)-trideca-2,6-dienyl ester

(2-trimethylethylsilylethoxy)methyl chloride

((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol

(E)-(2R,3R)-2-(4-Methoxy-benzyloxy)-3-methyl-oct-4-en-1-ol

Downstream raw materials:

Acetic acid (2E,6E)-(1R,4R,5S,11R)-1-[(E)-(1R,2R)-1-(4-methoxy-benzyloxy)-2-methyl-hept-3-enyl]-4,11-dimethyl-10-methylene-13-oxo-5-(2-trimethylsilanyl-ethoxymethoxy)-trideca-2,6-dienyl ester