5(4H)-Oxazolone, 4-[(1R,2E)-1-(acetyloxy)-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-buten yl]-4-[(dimethylphenylsilyl)methyl]-2-phenyl-, (4S)-

Base Information

• Chemical Name: 5(4H)-Oxazolone, 4-[(1R,2E)-1-(acetyloxy)-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-buten yl]-4-[(dimethylphenylsilyl)methyl]-2-phenyl-, (4S)-
• CAS No.: 389807-11-8
• Molecular Formula: C40H45NO5Si2
• Molecular Weight: 675.972
• Mol file: 389807-11-8.mol

Synonyms:

Chemical Property of 5(4H)-Oxazolone, 4-[(1R,2E)-1-(acetyloxy)-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-buten yl]-4-[(dimethylphenylsilyl)methyl]-2-phenyl-, (4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 5(4H)-Oxazolone, 4-[(1R,2E)-1-(acetyloxy)-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-buten yl]-4-[(dimethylphenylsilyl)methyl]-2-phenyl-, (4S)-

There total 9 articles about 5(4H)-Oxazolone, 4-[(1R,2E)-1-(acetyloxy)-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-buten yl]-4-[(dimethylphenylsilyl)methyl]-2-phenyl-, (4S)- 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: 68.0%

(E)-1,1-diacetoxy-4-(t-butyldiphenylsilyloxy)-2-butene (169689-20-7) + 2-phenyl-4-(dimethylphenylsilyl)methyl-4,5-dihydro-5-oxazolone (389807-44-7) → (1'R,4R,2'E)-4-[1'-acetoxy-4'-(tert-butyldiphenylsilyloxy)but-2'-en-1'-yl]-4-(dimethylphenylsilyl)methyl-2-phenyl-4,5-dihydro-5-oxazolone (389807-13-0) + (1'R,4S,2'E)-4-[1'-acetoxy-4'-(tert-butyldiphenylsilyloxy)but-2'-en-1'-yl]-4-(dimethylphenylsilyl)methyl-2-phenyl-4,5-dihydro-5-oxazolone (389807-11-8)

Guidance literature:

2-phenyl-4-(dimethylphenylsilyl)methyl-4,5-dihydro-5-oxazolone; With sodium hydride; In tetrahydrofuran; at 25 ℃; Irradiation;

With bis(η3-allyl-μ-chloropalladium(II)); (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; In tetrahydrofuran; at 25 ℃;

(E)-1,1-diacetoxy-4-(t-butyldiphenylsilyloxy)-2-butene; In tetrahydrofuran; at 0 ℃; for 3h; Further stages.;

DOI:10.1021/ja0118338

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (1'R,4S,2'E)-4-[1'-acetoxy-4'-(tert-butyldiphenylsilyloxy)but-2'-en-1'-yl]-4-(dimethylphenylsilyl)methyl-2-phenyl-4,5-dihydro-5-oxazolone (389807-11-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 98 percent / imidazole

2.1: 67 percent / PCC; Cellite / CH₂Cl₂

3.1: 99 percent / FeCl₃ / CH₂Cl₂ / 0 °C / 0.5 Torr

4.1: NaH / tetrahydrofuran / 25 °C / Irradiation

4.2: (η³-C3H5PdCl)2; (R,R)-1,2-(o-PPh2-C6H4-CO-NH)2-cyclohexane / tetrahydrofuran / 25 °C

4.3: 68 percent / tetrahydrofuran / 3 h / 0 °C

With 1H-imidazole; silica gel; iron(III) chloride; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja0118338

Reference yield:

N-benzoyl-2-bromoglycine methyl ester (101649-82-5) → (1'R,4S,2'E)-4-[1'-acetoxy-4'-(tert-butyldiphenylsilyloxy)but-2'-en-1'-yl]-4-(dimethylphenylsilyl)methyl-2-phenyl-4,5-dihydro-5-oxazolone (389807-11-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 61 percent / tetrahydrofuran / 3 h / -78 - 0 °C

2.1: 94 percent / LiOH / tetrahydrofuran; H₂O / 8 h / 25 °C

3.1: 97 percent / DCC / tetrahydrofuran / 12 h / 25 °C

4.1: NaH / tetrahydrofuran / 25 °C / Irradiation

4.2: (η³-C3H5PdCl)2; (R,R)-1,2-(o-PPh2-C6H4-CO-NH)2-cyclohexane / tetrahydrofuran / 25 °C

4.3: 68 percent / tetrahydrofuran / 3 h / 0 °C

With lithium hydroxide; sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; water;

DOI:10.1021/ja0118338

upstream raw materials:

(E)-1,1-diacetoxy-4-(t-butyldiphenylsilyloxy)-2-butene

2-phenyl-4-(dimethylphenylsilyl)methyl-4,5-dihydro-5-oxazolone

N-benzoyl-2-bromoglycine methyl ester

[(dimethylphenylsilyl)methyl]magnesium chloride

Downstream raw materials:

(2'E,1'S,6R,3aS,6aR)-6-[10',10'-ethylenedioxy-1'-(4-methoxybenzyloxy)-hexadec-2'-en-1'-yl]-3a-(4-methoxybenzyloxymethyl)-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

(1'S,3S,4S,5R)-3-benzamido-3-(4-methoxybenzyloxy)-4-acetoxy-5-[2'-(t-butyldiphenylsilyloxy)-1'-(4-methoxybenzyloxy)ethyl]oxolan-2-one

N-[(3S,4S,5S)-5-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-4-hydroxy-3-(4-methoxy-benzyloxymethyl)-2-oxo-tetrahydro-furan-3-yl]-benzamide

(1'S,6R,3aR,6aR)-6-[2'-t-butyldiphenylsilyloxy-1'-(4-methoxybenzyloxy)ethyl]-3a-(4-methoxybenzyloxymethyl)-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

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