317801-57-3

Basic information

• Product Name: (4R,5S)-(+)-3-[(2R)-2-isopropyl-5-methyl-1-oxohex-5-en-1-yl]-4-methyl-5-phenyl-2-oxazolidinone
• Synonyms: (4R,5S)-(+)-3-[(2R)-2-isopropyl-5-methyl-1-oxohex-5-en-1-yl]-4-methyl-5-phenyl-2-oxazolidinone
• CAS NO: 317801-57-3
• Molecular Weight: 329.439
• Mol File: 317801-57-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (4R,5S)-(+)-3-[(2R)-2-isopropyl-5-methyl-1-oxohex-5-en-1-yl]-4-methyl-5-phenyl-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5S)-(+)-3-[(2R)-2-isopropyl-5-methyl-1-oxohex-5-en-1-yl]-4-methyl-5-phenyl-2-oxazolidinone(317801-57-3)
• EPA Substance Registry System: (4R,5S)-(+)-3-[(2R)-2-isopropyl-5-methyl-1-oxohex-5-en-1-yl]-4-methyl-5-phenyl-2-oxazolidinone(317801-57-3)

Safety Data

• Hazardous Substances Data: 317801-57-3(Hazardous Substances Data)

Upstream product

• 109-72-8 n-butyllithium 
• 107599-99-5 (4R,5S)-(+)-3-[3-methyl-1-oxobut-1-yl]-4-methyl-5-phenyl-2-oxazolidinone 
• 154106-15-7 3-methylbut-3-en-1-yl trifluoromethanesulphonate 

Downstream Products

• 317801-55-1 (1S,2R)-2-isopropyl-5-methylidenecyclohexan-2-ol 
• 317801-55-1 (1R,2R)-2-isopropyl-5-methylidenecyclohexan-2-ol 
• 107599-99-5 (4R,5S)-(+)-3-[3-methyl-1-oxobut-1-yl]-4-methyl-5-phenyl-2-oxazolidinone 
• 106928-61-4 (1S,2R)-2-isopropyl-5-methylcyclohex-4-en-1-ol 
• 106928-60-3 (1R,2R)-2-isopropyl-5-methylcyclohex-4-en-1-ol 
• 77943-39-6 4-methyl-5-phenyloxazolidin-2-one 
• 317801-61-9 (R)-(+)-2-isopropyl-5-methylhex-5-ene-1-carboxylic acid 
• 264258-71-1 (R)-(+)-2-isopropyl-5-methylhex-5-en-1-ol 

Relevant articles and documents

Asymmetric synthesis and Lewis acid mediated type II carbonyl ene cyclisations of (R)-2-isopropyl-5-methylhex-5-enal

The asymmetric synthesis of (R)-2-isopropyl-5-methylhex-5-enal in 98% ee is described. It was discovered that the key alkylation step employing an Evans chiral auxiliary and 3-methylbut-3-en-1-yl trifluoromethanesulphonate as the alkylating agent led to significant competing O-alkylation, a phenomenon not previously reported. Type II carbonyl ene cyclisation of the aldehyde with a range of Lewis acids led to either the (R,R)- or (R,S)-5-methylidenecyclohexanols without concurrent racemisation of the alpha stereogenic centre of the aldehyde. Conditions for effecting the easy racemisation of a model enantiomerically pure aldehyde, (S)-2-methylbutanal, were developed. In an effort to secure a dynamic kinetic resolution procedure, these conditions were applied to (R)-2-isopropyl-5-methylhex-5-enal. However, a competing and dominant Prins cyclisation occurred instead leading to a mixture of all possible cycloadducts, all of which were obtained in 98% ee. Any unreacted aldehyde was found to be enantiomerically pure. Copyright (C) 2000 Elsevier Science Ltd.