4H-1,3-Oxazin-4-one, tetrahydro-6-phenyl-2-[(1S)-1-[[tris(1-methylethyl)silyl]oxy]ethyl]-, (2R,6S)-

Base Information

• Chemical Name: 4H-1,3-Oxazin-4-one, tetrahydro-6-phenyl-2-[(1S)-1-[[tris(1-methylethyl)silyl]oxy]ethyl]-, (2R,6S)-
• CAS No.: 823182-33-8
• Molecular Formula: C21H35NO3Si
• Molecular Weight: 377.59300
• Mol file: 823182-33-8.mol

Synonyms:(2R,6S)-6-Phenyl-2-((S)-1-triisopropylsilanyloxy-ethyl)-[1,3]oxazinan-4-one;

Chemical Property of 4H-1,3-Oxazin-4-one, tetrahydro-6-phenyl-2-[(1S)-1-[[tris(1-methylethyl)silyl]oxy]ethyl]-, (2R,6S)-

Chemical Property:

• PSA: 47.56000
• LogP: 5.49970

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4H-1,3-Oxazin-4-one, tetrahydro-6-phenyl-2-[(1S)-1-[[tris(1-methylethyl)silyl]oxy]ethyl]-, (2R,6S)-

There total 4 articles about 4H-1,3-Oxazin-4-one, tetrahydro-6-phenyl-2-[(1S)-1-[[tris(1-methylethyl)silyl]oxy]ethyl]-, (2R,6S)- 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: 98.0%

(2R,6S)-tert-butyl 2-((S)-1-triisopropylsilyloxyethyl)-4-oxo-6-phenyl-1,3-oxazinane-3-carboxylate (823182-39-4) → (2R,6S)-2-((S)-1-triisopropylsilyloxyethyl)-6-phenyl-1,3-oxazinan-4-one (823182-33-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.0833333h;

DOI:10.1016/j.tetasy.2004.09.009

Reference yield:

benzaldehyde (100-52-7) + C17H37NO2Si2 (823182-31-6) → (2R,6R)-2-[(S)-1-triisopropylsilyloxyethyl]-6-phenyl-[1,3]oxazinan-4-one + (2R,6S)-2-((S)-1-triisopropylsilyloxyethyl)-6-phenyl-1,3-oxazinan-4-one (823182-33-8) + (2S,6R)-2-((S)-1-triisopropylsilyloxyethyl)-6-phenyl-1,3-oxazinan-4-one + (2S,6S)-2-[(S)-1-triisopropylsilyloxyethyl]-6-phenyl-[1,3]oxazinan-4-one (823182-34-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃; for 8h; Title compound not separated from byproducts;

DOI:10.1016/j.tetasy.2004.09.009

Reference yield:

(2S)-2-(triisopropylsilyloxy)propionaldehyde (135614-60-7) → (2R,6S)-2-((S)-1-triisopropylsilyloxyethyl)-6-phenyl-1,3-oxazinan-4-one (823182-33-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hexane / 0.67 h / 0 °C

2.1: hexane / 1.25 h / 0 - 20 °C

2.2: triethylamine / hexane / 1.75 h / 0 - 20 °C

3.1: BF₃*Et₂O / CH₂Cl₂ / 8 h / -78 - 20 °C

With boron trifluoride diethyl etherate; In hexane; dichloromethane;

DOI:10.1016/j.tetasy.2004.09.009

upstream raw materials:

benzaldehyde

C₁₇H₃₇NO₂Si₂

(2R,6S)-tert-butyl 2-((S)-1-triisopropylsilyloxyethyl)-4-oxo-6-phenyl-1,3-oxazinane-3-carboxylate

(2S)-2-(triisopropylsilyloxy)propionaldehyde