2(S)-phenyl-1-<((1R,2S,5R)-8-phenylmenthoxy)carbonyl>-5-(triisopropylsilyl)-2,3-dihydro-4-pyridone

Base Information

• Chemical Name: 2(S)-phenyl-1-<((1R,2S,5R)-8-phenylmenthoxy)carbonyl>-5-(triisopropylsilyl)-2,3-dihydro-4-pyridone
• CAS No.: 126378-58-3
• Molecular Formula: C₃₇H₅₃NO₃Si
• Molecular Weight: 587.918

Synonyms:2(S)-phenyl-1-<((1R,2S,5R)-8-phenylmenthoxy)carbonyl>-5-(triisopropylsilyl)-2,3-dihydro-4-pyridone

Chemical Property of 2(S)-phenyl-1-<((1R,2S,5R)-8-phenylmenthoxy)carbonyl>-5-(triisopropylsilyl)-2,3-dihydro-4-pyridone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 2(S)-phenyl-1-<((1R,2S,5R)-8-phenylmenthoxy)carbonyl>-5-(triisopropylsilyl)-2,3-dihydro-4-pyridone

There total 9 articles about 2(S)-phenyl-1-<((1R,2S,5R)-8-phenylmenthoxy)carbonyl>-5-(triisopropylsilyl)-2,3-dihydro-4-pyridone 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:

(-)-8-phenylmenthol (65253-04-5) → 2(S)-phenyl-1-<((1R,2S,5R)-8-phenylmenthoxy)carbonyl>-5-(triisopropylsilyl)-2,3-dihydro-4-pyridone (126378-58-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / quinoline / toluene / 16 h / Ambient temperature

2: 1.) toluene, -23 deg C, 15 min, 2.) toluene, THF, -78 deg C, 1 h

With quinoline; In toluene;

DOI:10.1021/ja00090a019

Reference yield:

triisopropylsilyl chloride (13154-24-0) → 2(S)-phenyl-1-<((1R,2S,5R)-8-phenylmenthoxy)carbonyl>-5-(triisopropylsilyl)-2,3-dihydro-4-pyridone (126378-58-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA / 1.) THF, -23 deg C, 30 min, 2.) THF, RT, 12 h

2: 1.) toluene, -23 deg C, 15 min, 2.) toluene, THF, -78 deg C, 1 h

With lithium diisopropyl amide;

DOI:10.1021/ja00090a019

Reference yield:

4-Methoxy-1-[(1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyloxycarbonyl]-3-triisopropylsilanyl-pyridinium; chloride (144375-66-6) + phenylmagnesium chloride → (R)-4-Oxo-2-phenyl-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (126378-58-3,126378-59-4) + (S)-4-Oxo-2-phenyl-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (126378-58-3,126378-59-4)

Guidance literature:

In tetrahydrofuran; toluene; at -78 ℃; Yield given. Yields of byproduct given;

DOI:10.1021/jo00296a006

upstream raw materials:

4-Methoxy-1-[(1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyloxycarbonyl]-3-triisopropylsilanyl-pyridinium; chloride

4-methoxy-3-(trisopropylsilyl)pyridine

(-)-8-phenylmenthol chloroformate

(1R,2S,5R)-(-)-8-phenylmenthyl chloroformate

Downstream raw materials:

(2R)-2,3-dihydro-2-phenylpyridin-4(1H)-one

(2R,1'R,,2'S,5'R)-5'-methyl-2'-(1-methyl-1-phenylethyl)cyclohexyl 1,2,3,4-tetrahydro-4-oxo-2-phenylpyridine-1-carboxylate

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