(4S,5S,6R)-5-((tert-butyldimethylsilyl)oxy)-4-(4-methoxybenzyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine

Base Information

• Chemical Name: (4S,5S,6R)-5-((tert-butyldimethylsilyl)oxy)-4-(4-methoxybenzyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine
• CAS No.: 1575517-60-0
• Molecular Formula: C₂₆H₃₅NO₃Si
• Molecular Weight: 437.654
• Mol file: 1575517-60-0.mol

Synonyms:(4S,5S,6R)-5-((tert-butyldimethylsilyl)oxy)-4-(4-methoxybenzyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine

Chemical Property of (4S,5S,6R)-5-((tert-butyldimethylsilyl)oxy)-4-(4-methoxybenzyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S,6R)-5-((tert-butyldimethylsilyl)oxy)-4-(4-methoxybenzyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine

There total 2 articles about (4S,5S,6R)-5-((tert-butyldimethylsilyl)oxy)-4-(4-methoxybenzyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine 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:

N-((2S,3R,E)-3-((tert-butyldimethylsilyl)oxy)-6-chloro-1-(4-methoxyphenyl)hex-4-en-2-yl)benzamide (1575517-24-6) → (4S,5S,6S)-5-((tert-butyldimethylsilyl)oxy)-4-(4-methoxybenzyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine (1575517-26-8) + (4S,5S,6R)-5-((tert-butyldimethylsilyl)oxy)-4-(4-methoxybenzyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine (1575517-60-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 12h; Overall yield = 72 %; Overall yield = 246 mg; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2014.02.033

Reference yield:

C20H22ClNO3 + tert-butyldimethylsilyl chloride (18162-48-6) → (4S,5S,6S)-5-((tert-butyldimethylsilyl)oxy)-4-(4-methoxybenzyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine (1575517-26-8) + (4S,5S,6R)-5-((tert-butyldimethylsilyl)oxy)-4-(4-methoxybenzyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine (1575517-60-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

2: tetra-(n-butyl)ammonium iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride / tetrahydrofuran; mineral oil / 12 h / 0 °C / Inert atmosphere

With 1H-imidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.tet.2014.02.033

upstream raw materials:

tert-butyldimethylsilyl chloride

N-((2S,3R,E)-3-((tert-butyldimethylsilyl)oxy)-6-chloro-1-(4-methoxyphenyl)hex-4-en-2-yl)benzamide