(4E,9E,13E)-(6R,7R,8R,11R,12S,18R)-7-(4-Methoxy-benzyloxy)-6,11,18-trimethyl-17-methylene-20-(tetrahydro-pyran-2-yloxy)-12-(2-trimethylsilanyl-ethoxymethoxy)-icosa-4,9,13-trien-8-ol

Base Information

• Chemical Name: (4E,9E,13E)-(6R,7R,8R,11R,12S,18R)-7-(4-Methoxy-benzyloxy)-6,11,18-trimethyl-17-methylene-20-(tetrahydro-pyran-2-yloxy)-12-(2-trimethylsilanyl-ethoxymethoxy)-icosa-4,9,13-trien-8-ol
• CAS No.: 216494-37-0
• Molecular Formula: C₄₃H₇₂O₇Si
• Molecular Weight: 729.126
• Mol file: 216494-37-0.mol

Synonyms:(4E,9E,13E)-(6R,7R,8R,11R,12S,18R)-7-(4-Methoxy-benzyloxy)-6,11,18-trimethyl-17-methylene-20-(tetrahydro-pyran-2-yloxy)-12-(2-trimethylsilanyl-ethoxymethoxy)-icosa-4,9,13-trien-8-ol

Chemical Property of (4E,9E,13E)-(6R,7R,8R,11R,12S,18R)-7-(4-Methoxy-benzyloxy)-6,11,18-trimethyl-17-methylene-20-(tetrahydro-pyran-2-yloxy)-12-(2-trimethylsilanyl-ethoxymethoxy)-icosa-4,9,13-trien-8-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4E,9E,13E)-(6R,7R,8R,11R,12S,18R)-7-(4-Methoxy-benzyloxy)-6,11,18-trimethyl-17-methylene-20-(tetrahydro-pyran-2-yloxy)-12-(2-trimethylsilanyl-ethoxymethoxy)-icosa-4,9,13-trien-8-ol

There total 14 articles about (4E,9E,13E)-(6R,7R,8R,11R,12S,18R)-7-(4-Methoxy-benzyloxy)-6,11,18-trimethyl-17-methylene-20-(tetrahydro-pyran-2-yloxy)-12-(2-trimethylsilanyl-ethoxymethoxy)-icosa-4,9,13-trien-8-ol 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:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → (4E,9E,13E)-(6R,7R,8R,11R,12S,18R)-7-(4-Methoxy-benzyloxy)-6,11,18-trimethyl-17-methylene-20-(tetrahydro-pyran-2-yloxy)-12-(2-trimethylsilanyl-ethoxymethoxy)-icosa-4,9,13-trien-8-ol (216494-37-0)

Guidance literature:

Multi-step reaction with 7 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

With 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; 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) → (4E,9E,13E)-(6R,7R,8R,11R,12S,18R)-7-(4-Methoxy-benzyloxy)-6,11,18-trimethyl-17-methylene-20-(tetrahydro-pyran-2-yloxy)-12-(2-trimethylsilanyl-ethoxymethoxy)-icosa-4,9,13-trien-8-ol (216494-37-0)

Guidance literature:

Multi-step reaction with 9 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

With 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; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja982572d

Reference yield:

2,2-Dimethyl-propionic acid (2R,3R)-4-hydroxy-2-(4-methoxy-benzyloxy)-3-methyl-butyl ester → (4E,9E,13E)-(6R,7R,8R,11R,12S,18R)-7-(4-Methoxy-benzyloxy)-6,11,18-trimethyl-17-methylene-20-(tetrahydro-pyran-2-yloxy)-12-(2-trimethylsilanyl-ethoxymethoxy)-icosa-4,9,13-trien-8-ol (216494-37-0)

Guidance literature:

Multi-step reaction with 5 steps

1: CrCl₂ / tetrahydrofuran

2: (PPh₃)4Pd / Ambient temperature

3: MeLi / diethyl ether

4: 1.) (COCl)2, DMSO, 2.) Et₃N

5: 1.) t-BuLi, 2.) Me₂Zn

With chromium dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; methyllithium; dimethyl zinc(II); tert.-butyl lithium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ja982572d

upstream raw materials:

(E)-(2R,3R)-2-(4-Methoxy-benzyloxy)-3-methyl-oct-4-enal

{2-[(E)-(1S,7R)-1-((E)-(R)-3-Iodo-1-methyl-allyl)-7-methyl-6-methylene-9-(tetrahydro-pyran-2-yloxy)-non-2-enyloxymethoxy]-ethyl}-trimethyl-silane

(2-trimethylethylsilylethoxy)methyl chloride

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

Downstream raw materials:

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

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