(5R,6S)-2-methyl-2-phenylsulfanyl-5-hydroxy-6-(tert-butyldimethylsilyloxy)heptan-3-one

Base Information

• Chemical Name: (5R,6S)-2-methyl-2-phenylsulfanyl-5-hydroxy-6-(tert-butyldimethylsilyloxy)heptan-3-one
• CAS No.: 312326-73-1
• Molecular Formula: C₂₀H₃₄O₃SSi
• Molecular Weight: 382.64
• Mol file: 312326-73-1.mol

Synonyms:(5R,6S)-2-methyl-2-phenylsulfanyl-5-hydroxy-6-(tert-butyldimethylsilyloxy)heptan-3-one

Chemical Property of (5R,6S)-2-methyl-2-phenylsulfanyl-5-hydroxy-6-(tert-butyldimethylsilyloxy)heptan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6S)-2-methyl-2-phenylsulfanyl-5-hydroxy-6-(tert-butyldimethylsilyloxy)heptan-3-one

There total 4 articles about (5R,6S)-2-methyl-2-phenylsulfanyl-5-hydroxy-6-(tert-butyldimethylsilyloxy)heptan-3-one 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: 32.0%

2-methyl-2-phenylsulfanylbutan-3-one (35875-02-6) + (S)-2-tert-butyl-dimethyl-silanyloxy propanal (87727-28-4) → (5R,6S)-2-methyl-2-phenylsulfanyl-5-hydroxy-6-(tert-butyldimethylsilyloxy)heptan-3-one (312326-73-1) + (5S,6S)-2-methyl-2-phenylsulfanyl-5-hydroxy-6-(tert-butyldimethylsilyloxy)heptan-3-one (312326-74-2)

Guidance literature:

2-methyl-2-phenylsulfanylbutan-3-one; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

(S)-2-tert-butyl-dimethyl-silanyloxy propanal; In tetrahydrofuran;

DOI:10.1039/b005336h

Reference yield:

(2RS)-3-methyl-3-phenylsulfanylbutan-2-ol (58468-92-1) → (5R,6S)-2-methyl-2-phenylsulfanyl-5-hydroxy-6-(tert-butyldimethylsilyloxy)heptan-3-one (312326-73-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 87 percent / pyridinium chlorochromate / CH₂Cl₂ / 20 °C

2.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: tetrahydrofuran; hexane / 2 h / -78 °C

With pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1039/b208558e

Reference yield:

2-methyl-2-(phenylthio)propanal (63996-66-7) → (5R,6S)-2-methyl-2-phenylsulfanyl-5-hydroxy-6-(tert-butyldimethylsilyloxy)heptan-3-one (312326-73-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 99 percent / diethyl ether / 1 h / 20 °C

2.1: 87 percent / pyridinium chlorochromate / CH₂Cl₂ / 20 °C

3.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: tetrahydrofuran; hexane / 2 h / -78 °C

With pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1039/b208558e

upstream raw materials:

2-methyl-2-phenylsulfanylbutan-3-one

(S)-2-tert-butyl-dimethyl-silanyloxy propanal

(2RS)-3-methyl-3-phenylsulfanylbutan-2-ol

2-methyl-2-(phenylthio)propanal

Downstream raw materials:

(2S,3R,5S)-6-Methyl-6-phenylsulfanyl-heptane-2,3,5-triol

(3R,5R,6S)-2-methyl-2-phenylsulfanyl-6-(tert-butyldimethylsiloxy)heptane-3,5-diol