Acetic acid, [[(1S,2R)-2-[(4-methoxyphenyl)methoxy]-1-methyl-1-[2-[[tris(1-methyleth yl)silyl]oxy]ethyl]-4-pentenyl]oxy]-

Base Information

• Chemical Name: Acetic acid, [[(1S,2R)-2-[(4-methoxyphenyl)methoxy]-1-methyl-1-[2-[[tris(1-methyleth yl)silyl]oxy]ethyl]-4-pentenyl]oxy]-
• CAS No.: 874660-43-2
• Molecular Formula: C27H46O6Si
• Molecular Weight: 494.744
• Mol file: 874660-43-2.mol

Synonyms:

Chemical Property of Acetic acid, [[(1S,2R)-2-[(4-methoxyphenyl)methoxy]-1-methyl-1-[2-[[tris(1-methyleth yl)silyl]oxy]ethyl]-4-pentenyl]oxy]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid, [[(1S,2R)-2-[(4-methoxyphenyl)methoxy]-1-methyl-1-[2-[[tris(1-methyleth yl)silyl]oxy]ethyl]-4-pentenyl]oxy]-

There total 8 articles about Acetic acid, [[(1S,2R)-2-[(4-methoxyphenyl)methoxy]-1-methyl-1-[2-[[tris(1-methyleth yl)silyl]oxy]ethyl]-4-pentenyl]oxy]- 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: 84.0%

C25H44O4Si + bromoacetic acid (79-08-3) → [(1S,2R)-2-(4-Methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-acetic acid (874660-43-2)

Guidance literature:

bromoacetic acid; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; Inert atmosphere;

C₂₅H₄₄O₄Si; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1002/chem.200900776

Reference yield: 73.0%

(3S,4R)-4-(4-Methoxy-benzyloxy)-3-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol (874660-20-5) + bromoacetic acid (79-08-3) → [(1S,2R)-2-(4-Methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-acetic acid (874660-43-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1021/ol0526625

Reference yield:

(R)-4-(4-Methoxy-benzyloxy)-hept-6-ene-1,3-diol (874660-41-0) → [(1S,2R)-2-(4-Methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-acetic acid (874660-43-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / imidazole / dimethylformamide / 0 - 20 °C

2: 96 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 1 h

3: 95 percent / tetrahydrofuran; diethyl ether / -78 °C

4: 73 percent / sodium hydride / tetrahydrofuran; dimethylformamide / 0 - 20 °C

With pyridine; 1H-imidazole; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0526625

upstream raw materials:

(3S,4R)-4-(4-Methoxy-benzyloxy)-3-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol

bromoacetic acid

(R)-4-(4-Methoxy-benzyloxy)-hept-6-ene-1,3-diol

3-hydroxy-4-(4-methoxy-benzyloxy)-hept-6-enoic acid tert-butyl ester

Downstream raw materials:

(R)-3-Benzyloxy-2-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-propionaldehyde

(S)-3-Benzyloxy-2-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-propan-1-ol

(S)-4-Isopropyl-3-{2-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-acetyl}-oxazolidin-2-one

(R)-5-Benzyloxy-4-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-1-(2-triisopropylsilanyloxy-ethyl)-pent-4-enyloxy]-pent-1-en-3-ol

Refernces

• 1、 Crimmins, Michael T.,Zuccarello, J. Lucas,Cleary, Pamela A.,Parrish, Jonathan D.. "Convergent, stereoselective synthesis of the GHIJ fragment of brevetoxin A". . p. 159 - 162. Retrieved 2007/10/03.