(4S,5S)-4-((1S,2S)-1-Hydroxy-2-methyl-but-3-enyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Base Information

Chemical Name:(4S,5S)-4-((1S,2S)-1-Hydroxy-2-methyl-but-3-enyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester
CAS No.:148843-20-3
Molecular Formula:C₁₉H₂₅NO₄
Molecular Weight:331.412
Hs Code.:

Synonyms:(4S,5S)-4-((1S,2S)-1-Hydroxy-2-methyl-but-3-enyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4S,5S)-4-((1S,2S)-1-Hydroxy-2-methyl-but-3-enyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

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Technology Process of (4S,5S)-4-((1S,2S)-1-Hydroxy-2-methyl-but-3-enyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

There total 8 articles about (4S,5S)-4-((1S,2S)-1-Hydroxy-2-methyl-but-3-enyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 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:

: 148906-20-1
(4R,5S)-5-isopropyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester

: 148843-20-3
(4S,5S)-4-((1S,2S)-1-Hydroxy-2-methyl-but-3-enyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) LHMDS / 1.) THF, -78 deg C, 1 h, 2.) THF, Et₂O, -78 deg C, 10 min

2: DCC, TFA, pyridine / benzene; dimethylsulfoxide / Ambient temperature

3: 1.) tert-BuOK, n-BuLi, 2.) (-)-B-methoxy-(diisopinocampheyl)borane, 3.) BF₃*Et₂O

With pyridine; n-butyllithium; boron trifluoride diethyl etherate; potassium tert-butylate; dicyclohexyl-carbodiimide; (-)-B-methoxydiisopinocampheylborane; trifluoroacetic acid; lithium hexamethyldisilazane; In dimethyl sulfoxide; benzene;
DOI:10.1021/ja9541544

Reference yield:

: 148843-18-9
(4S,5S)-4-Hydroxymethyl-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

: 148843-20-3
(4S,5S)-4-((1S,2S)-1-Hydroxy-2-methyl-but-3-enyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: DCC, TFA, pyridine / benzene; dimethylsulfoxide / Ambient temperature

2: 1.) tert-BuOK, n-BuLi, 2.) (-)-B-methoxy-(diisopinocampheyl)borane, 3.) BF₃*Et₂O

With pyridine; n-butyllithium; boron trifluoride diethyl etherate; potassium tert-butylate; dicyclohexyl-carbodiimide; (-)-B-methoxydiisopinocampheylborane; trifluoroacetic acid; In dimethyl sulfoxide; benzene;
DOI:10.1021/ja9541544

Reference yield:

: (2R,3S)-3-hydroxyleucine methyl ester hydrochloride

: 148843-20-3
(4S,5S)-4-((1S,2S)-1-Hydroxy-2-methyl-but-3-enyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 82 percent / p-TsOH*H₂O / 1,2-dimethoxy-ethane / 3.5 h / Heating

2: 1.) LHMDS / 1.) THF, -78 deg C, 1 h, 2.) THF, Et₂O, -78 deg C, 10 min

3: DCC, TFA, pyridine / benzene; dimethylsulfoxide / Ambient temperature

4: 1.) tert-BuOK, n-BuLi, 2.) (-)-B-methoxy-(diisopinocampheyl)borane, 3.) BF₃*Et₂O

With pyridine; n-butyllithium; boron trifluoride diethyl etherate; potassium tert-butylate; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; (-)-B-methoxydiisopinocampheylborane; trifluoroacetic acid; lithium hexamethyldisilazane; In 1,2-dimethoxyethane; dimethyl sulfoxide; benzene;
DOI:10.1021/ja9541544