(5S)-1-[(4S)-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)]-5-(triisopropylsilyloxy)-2-trimethylsilyloxy-3-azahexa-1,3-diene

Base Information

• Chemical Name: (5S)-1-[(4S)-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)]-5-(triisopropylsilyloxy)-2-trimethylsilyloxy-3-azahexa-1,3-diene
• CAS No.: 198147-93-2
• Molecular Formula: C₂₆H₄₄N₂O₄Si₂
• Molecular Weight: 504.817
• Mol file: 198147-93-2.mol

Synonyms:(5S)-1-[(4S)-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)]-5-(triisopropylsilyloxy)-2-trimethylsilyloxy-3-azahexa-1,3-diene

Chemical Property of (5S)-1-[(4S)-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)]-5-(triisopropylsilyloxy)-2-trimethylsilyloxy-3-azahexa-1,3-diene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S)-1-[(4S)-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)]-5-(triisopropylsilyloxy)-2-trimethylsilyloxy-3-azahexa-1,3-diene

There total 5 articles about (5S)-1-[(4S)-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)]-5-(triisopropylsilyloxy)-2-trimethylsilyloxy-3-azahexa-1,3-diene 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:

2-(4(S)-phenyloxazolidin-2-on-3-yl)acetyl chloride (99333-55-8) + (2S)-2-(triisopropylsiloxy)-N-(trimethylsilyl)propanimine (160067-44-7) → (5S)-1-[(4S)-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)]-5-(triisopropylsilyloxy)-2-trimethylsilyloxy-3-azahexa-1,3-diene (198147-93-2)

Guidance literature:

With triethylamine; In n-heptane; toluene; 0 deg C, 30 min; rt, 1 h;

DOI:10.1021/jo971395g

Reference yield:

(2S)-2-(triisopropylsilyloxy)propionaldehyde (135614-60-7) → (5S)-1-[(4S)-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)]-5-(triisopropylsilyloxy)-2-trimethylsilyloxy-3-azahexa-1,3-diene (198147-93-2)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium bis(trimethylsilyl)amide / heptane; hexane / 1 h / 0 °C

2: heptane / 0 - 20 °C

3: Et₃N / heptane; toluene / 0 - 20 °C

With triethylamine; lithium hexamethyldisilazane; In hexane; n-heptane; toluene;

DOI:10.1016/S0957-4166(01)00051-9

Reference yield:

2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetic acid (123882-32-6,136861-61-5,99333-54-7) → (5S)-1-[(4S)-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)]-5-(triisopropylsilyloxy)-2-trimethylsilyloxy-3-azahexa-1,3-diene (198147-93-2)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride

2: Et₃N / heptane; toluene / 0 - 20 °C

With oxalyl dichloride; triethylamine; In n-heptane; toluene;

DOI:10.1016/S0957-4166(01)00051-9

upstream raw materials:

2-(4(S)-phenyloxazolidin-2-on-3-yl)acetyl chloride

(2S)-2-(triisopropylsiloxy)-N-(trimethylsilyl)propanimine

N-trimethylsilylimine of 2(S)-(triisopropylsilyloxy)lactaldehyde

2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetic acid

Downstream raw materials:

[(2R,5R,6S)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-oxo-2-((S)-1-triisopropylsilanyloxy-ethyl)-[1,3]oxazinan-5-yl]-carbamic acid benzyl ester

[(2R,5R)-4-oxo-2-[(1S)-triisopropylsilanyloxyethyl]-[1,3]oxazinan-5-yl]carbamic acid benzyl ester

(5R)-[(4S)-(2-oxo-4-phenyloxazolidin-3-yl)]-(2R)-(1S-triisopropylsilanyloxyethyl)-[1,3]oxazinan-4-one