phenylsulfanyl-acetic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyl ester

Base Information

• Chemical Name: phenylsulfanyl-acetic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyl ester
• CAS No.: 851592-83-1
• Molecular Formula: C₃₀H₃₆O₃SSi
• Molecular Weight: 504.766
• Mol file: 851592-83-1.mol

Synonyms:phenylsulfanyl-acetic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyl ester

Chemical Property of phenylsulfanyl-acetic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenylsulfanyl-acetic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyl ester

There total 1 articles about phenylsulfanyl-acetic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyl 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: 86.0%

(phenylthio)acetic acid (103-04-8) + (3S)-1-{[t-butyl(diphenyl)silyl]oxy}hex-5-en-3-ol (112897-09-3) → phenylsulfanyl-acetic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyl ester (851592-83-1)

Guidance literature:

With dicyclohexyl-carbodiimide; 4-(dimethylamino)pyridinium tosylate; In dichloromethane;

DOI:10.1021/ol050270s

Reference yield: 94.0%

phenylsulfanyl-acetic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyl ester (851592-83-1) + 3-Methoxymethoxy-2-methyl-propionaldehyde → 3-hydroxy-5-methoxymethoxy-4-methyl-2-phenylsulfanyl-pentanoic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyl ester (851770-88-2)

Guidance literature:

phenylsulfanyl-acetic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyl ester; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃;

3-Methoxymethoxy-2-methyl-propionaldehyde; In tetrahydrofuran; hexane; at -78 - -35 ℃;

DOI:10.1021/ol050270s

Reference yield:

phenylsulfanyl-acetic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyl ester (851592-83-1) → 1-{1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyloxy}-2-(5-methyl-6H-[1,3]dioxin-4-yl)-ethanol

Guidance literature:

Multi-step reaction with 6 steps

1.1: LDA / tetrahydrofuran; hexane / -78 °C

1.2: 94 percent / tetrahydrofuran; hexane / -78 - -35 °C

2.1: BF₃*OEt₂ / CH₂Cl₂ / 0.25 h / 0 °C

3.1: 91 percent / m-CPBA / CH₂Cl₂ / 0.42 h / -78 °C

4.1: 22 percent / P(OEt)3 / m-xylene / 1 h / Heating

5.1: 76 percent / NaHMDS / tetrahydrofuran / 0.02 h / -78 °C

6.1: DIBAL-H / CH₂Cl₂; hexane / 0.83 h / -78 °C

With boron trifluoride diethyl etherate; sodium hexamethyldisilazane; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; triethyl phosphite; In tetrahydrofuran; hexane; dichloromethane; m-xylene;

DOI:10.1021/ol050270s

upstream raw materials:

(phenylthio)acetic acid

(3S)-1-{[t-butyl(diphenyl)silyl]oxy}hex-5-en-3-ol

Downstream raw materials:

3-hydroxy-5-methoxymethoxy-4-methyl-2-phenylsulfanyl-pentanoic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyl ester

(5-methyl-[1,3]dioxan-4-ylidene)-acetic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyl ester

(2S,3S,6R)-6-Allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-one

(5-methyl-6H-[1,3]dioxin-4-yl)-acetic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyl ester