(3R,4S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-methylene-2-oxo-3-(3-trimethylsilanyl-but-3-enyl)-octanoic acid methyl ester

Base Information

• Chemical Name: (3R,4S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-methylene-2-oxo-3-(3-trimethylsilanyl-but-3-enyl)-octanoic acid methyl ester
• CAS No.: 873297-62-2
• Molecular Formula: C₃₁H₅₂O₅Si₂
• Molecular Weight: 560.922
• Mol file: 873297-62-2.mol

Synonyms:(3R,4S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-methylene-2-oxo-3-(3-trimethylsilanyl-but-3-enyl)-octanoic acid methyl ester

Chemical Property of (3R,4S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-methylene-2-oxo-3-(3-trimethylsilanyl-but-3-enyl)-octanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-methylene-2-oxo-3-(3-trimethylsilanyl-but-3-enyl)-octanoic acid methyl ester

There total 1 articles about (3R,4S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-methylene-2-oxo-3-(3-trimethylsilanyl-but-3-enyl)-octanoic acid methyl 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: 64.0%

(E)-2-{5-Benzyloxy-2-[2-(tert-butyl-dimethyl-silanyloxy)-eth-(Z)-ylidene]-pentyloxy}-6-trimethylsilanyl-hepta-2,6-dienoic acid methyl ester → (Z)-2-{5-Benzyloxy-2-[2-(tert-butyl-dimethyl-silanyloxy)-eth-(Z)-ylidene]-pentyloxy}-6-trimethylsilanyl-hepta-2,6-dienoic acid methyl ester + (3R,4S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-methylene-2-oxo-3-(3-trimethylsilanyl-but-3-enyl)-octanoic acid methyl ester (873297-62-2)

Guidance literature:

[Cu((S,S)-((CH₃)3CCHCH₂OCN)2C(CH₃)2)(H₂O)2](SbF₆)2; In dichloromethane; at 20 ℃; for 27h;

DOI:10.1021/ol052462t

Reference yield: 68.0%

(3R,4S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-methylene-2-oxo-3-(3-trimethylsilanyl-but-3-enyl)-octanoic acid methyl ester (873297-62-2) + Methyltriphenylphosphonium bromide (1779-49-3) → 3-[2-(3-benzyloxy-propyl)-1-(tert-butyl-dimethyl-silanyloxymethyl)-allyl]-2-methylene-6-trimethylsilanyl-hept-6-enoic acid methyl ester (873297-69-9)

Guidance literature:

Methyltriphenylphosphonium bromide; With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 1h;

(3R,4S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-methylene-2-oxo-3-(3-trimethylsilanyl-but-3-enyl)-octanoic acid methyl ester; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ol052462t

Reference yield:

(3R,4S)-8-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-methylene-2-oxo-3-(3-trimethylsilanyl-but-3-enyl)-octanoic acid methyl ester (873297-62-2) → (4R,5S)-5-(4-Benzyloxy-1-methylene-butyl)-3-methylene-4-(3-trimethylsilanyl-but-3-enyl)-tetrahydro-pyran-2-one

Guidance literature:

Multi-step reaction with 2 steps

1.1: LiHMDS / tetrahydrofuran / 1 h / 0 °C

1.2: 68 percent / tetrahydrofuran / 0 - 20 °C

2.1: 77 percent / HF*pyridine / tetrahydrofuran / 16 h / 20 °C

With pyridine hydrogenfluoride; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1021/ol052462t

Downstream raw materials:

3-[2-(3-benzyloxy-propyl)-1-(tert-butyl-dimethyl-silanyloxymethyl)-allyl]-2-methylene-6-trimethylsilanyl-hept-6-enoic acid methyl ester