65534-62-5

Basic information

• Product Name: (3R^*,5S^*)-2,6-dimethyl-3,5-heptanediol
• Synonyms: (3R^*,5S^*)-2,6-dimethyl-3,5-heptanediol
• CAS NO: 65534-62-5
• Molecular Weight: 160.257
• Mol File: 65534-62-5.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: (3R^*,5S^*)-2,6-dimethyl-3,5-heptanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R^*,5S^*)-2,6-dimethyl-3,5-heptanediol(65534-62-5)
• EPA Substance Registry System: (3R^*,5S^*)-2,6-dimethyl-3,5-heptanediol(65534-62-5)

Safety Data

• Hazardous Substances Data: 65534-62-5(Hazardous Substances Data)

Upstream product

• 65429-68-7 5-hydroxy-2,6-dimethyl-heptan-3-one 
• 105627-17-6 2,2,4,6-tetraisopropyl-1,3-dioxa-2-silacyclohexene 
• 75-09-2 dichloromethane 
• 78-84-2 isobutyraldehyde 
• 18362-64-6 2,6-dimethyl-3,5-heptanedione 
• 107-11-9 1-amino-2-propene 
• 870-63-3 prenyl bromide 
• 116212-25-0 2,2-Dimethyl-3-<3-methyl-2-(trimethylsilyloxy)butyl>oxirane 
• 132047-52-0 1,1-Dibromo-4-methyl-3-(trimethylsilyloxy)pentane 
• 132157-15-4 5,5-Dibromo-2-methyl-2-pentene 
• 142321-70-8 1,1-Dibromo-4-methyl-3-pentanol 
• 105627-13-2 2,6-dimethyl-5-di-isopropylsilyloxyheptan-3-one 
• 36587-79-8 5-hydroxy-2,5-dimethyl-3-hexanone 
• 563-80-4 3-methyl-butan-2-one 

Downstream Products

• 816455-38-6 (1S,2R,3S,4R,5R,6R)-5-Bromo-6-((1R,3S)-3-hydroxy-1-isopropyl-4-methyl-pentyloxy)-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde 
• 816455-41-1 (1S,2R,3S,4R,5R,6R)-5-Bromo-6-[(1R,3S)-3-(tert-butyl-diphenyl-silanyloxy)-1-isopropyl-4-methyl-pentyloxy]-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde 
• 2344-70-9 1-phenyl-3-butanol 
• 1243579-23-8 2,6-dimethyl-5-octylsulfanylheptan-3-one 
• 125787-42-0 (3S,5R)-5-(Cyclohex-1-enyloxy)-2,6-dimethyl-heptan-3-ol 
• 375347-35-6 (3S,5R)-5-benzyloxy-2,6-dimethyl-3-heptanol 
• 375347-24-3 (2S,4R,6S)-4,6-Diisopropyl-2-methoxy-[1,3]dioxane 

Relevant articles and documents

Reduction of β-Hydroxy Ketones with Catecholborane. A Stereoselective Approach to the Synthesis of Syn 1,3-Diols

The stereoselective reduction of acyclic β-hydroxy ketones to syn 1,3-diols may be achieved with the mild reducing agent catecholborane.In certain instances reaction stereoselectivity may be enhanced through rhodium(I) catalysis.

The zirconium alkoxide-catalyzed aldol-tishchenko reaction of ketone aldols

The aldol-Tishchenko reaction of ketone aldols as enol equivalents has been developed as an efficient strategy to furnish differentiated 1,3-anti-diol monoesters in one step. The thermodynamically unstable ketone aldols undergo a facile retro-aldolization to yield a presumed zirconium enolate in situ, which then undergoes the aldol-Tishchenko reaction in typically high yields and with complete 1,3-anti diastereocontrol. Evaluation of a broad range of metal alkoxides as catalysts and optimization of the reaction protocol led to a modified zirconium alkoxide catalyst with attenuated Lewis acidity and dichloromethane as solvent, which resulted in suppression of the undesired acyl migration to a large extent. Various ketone aldols have been prepared and subjected to the general process, giving rise to a broad range of differently substituted 1,3-anti-diol monoesters, which may be hydrolyzed to the corresponding 1,3-anti-diols.

Stereocontrolled reductive amination of 3-hydroxy ketones

syn-1,3-Aminoalcohols are synthesized in high diastereomeric excess by reductive amination of 3-hydroxyketones with sodium cyanoborohydride in the presence of benzylamine.