(2S,3R,4S,8S)-1-[(S)-4-benzyl-2-oxo-oxazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-2,4,8-trimethylnon-5-ene-1,7-dione

Base Information

• Chemical Name: (2S,3R,4S,8S)-1-[(S)-4-benzyl-2-oxo-oxazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-2,4,8-trimethylnon-5-ene-1,7-dione
• CAS No.: 845522-61-4
• Molecular Formula: C₃₆H₅₁NO₇Si
• Molecular Weight: 637.889
• Mol file: 845522-61-4.mol

Synonyms:(2S,3R,4S,8S)-1-[(S)-4-benzyl-2-oxo-oxazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-2,4,8-trimethylnon-5-ene-1,7-dione

Chemical Property of (2S,3R,4S,8S)-1-[(S)-4-benzyl-2-oxo-oxazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-2,4,8-trimethylnon-5-ene-1,7-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,8S)-1-[(S)-4-benzyl-2-oxo-oxazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-2,4,8-trimethylnon-5-ene-1,7-dione

There total 1 articles about (2S,3R,4S,8S)-1-[(S)-4-benzyl-2-oxo-oxazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-2,4,8-trimethylnon-5-ene-1,7-dione 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%

(3S)-dimethyl [4-(4-methoxybenzyloxy)-3-methyl-2-oxobutyl]phosphonate + (2R,3R,4S)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-5-oxo-pentanal (812649-72-2) → (2S,3R,4S,8S)-1-[(S)-4-benzyl-2-oxo-oxazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-2,4,8-trimethylnon-5-ene-1,7-dione (845522-61-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; at 20 ℃;

DOI:10.1021/ol0478178

Reference yield: 76.0%

lithium dimethylcuprate (15681-48-8) + (2S,3R,4S,8S)-1-[(S)-4-benzyl-2-oxo-oxazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-2,4,8-trimethylnon-5-ene-1,7-dione (845522-61-4) → (2S,3R,4S,5R,6RS)-3-(tert-butyldimethylsilyloxy)-6-[3-(4-methoxybenzyloxy)-2-methylpropionyl]-2,4,5-trimethylcyclohexanone (845522-60-3)

Guidance literature:

With dimethylsulfide; In diethyl ether;

DOI:10.1021/ol0478178

Reference yield:

(2S,3R,4S,8S)-1-[(S)-4-benzyl-2-oxo-oxazolidin-3-yl]-3-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-2,4,8-trimethylnon-5-ene-1,7-dione (845522-61-4) → (2RS)-2-methyl-3-oxo-3-[(1S,5S,6R)-1,3,5,6-tetramethyl-2-oxocyclohex-3-enyl]propionic acid (845522-58-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 76 percent / Me₂S / diethyl ether

2.1: NaH / tetrahydrofuran / 17 h / 20 °C

2.2: 96 percent / DDQ / CH₂Cl₂ / 0 °C / pH 7

3.1: Dess-Martin periodinane / CH₂Cl₂

4.1: 64 percent / NaClO₂; NaH₂PO₄; Me₂C=CHMe / 2-methyl-propan-2-ol; H₂O

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; dimethylsulfide; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/ol0478178

upstream raw materials:

(2R,3R,4S)-5-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-5-oxo-pentanal

Downstream raw materials:

(2S,3R,4S,5R,6RS)-3-(tert-butyldimethylsilyloxy)-6-[3-(4-methoxybenzyloxy)-2-methylpropionyl]-2,4,5-trimethylcyclohexanone

(2RS)-2-methyl-3-oxo-3-[(1S,5S,6R)-1,3,5,6-tetramethyl-2-oxocyclohex-3-enyl]propionic acid