608136-22-7

Basic information

• Product Name: (R)-2-acetoxy-5-benzyloxy-1-(tert-butyldimethylsilyloxy)pentane
• Synonyms: (R)-2-acetoxy-5-benzyloxy-1-(tert-butyldimethylsilyloxy)pentane
• CAS NO: 608136-22-7
• Molecular Weight: 366.573
• Mol File: 608136-22-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-2-acetoxy-5-benzyloxy-1-(tert-butyldimethylsilyloxy)pentane(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-acetoxy-5-benzyloxy-1-(tert-butyldimethylsilyloxy)pentane(608136-22-7)
• EPA Substance Registry System: (R)-2-acetoxy-5-benzyloxy-1-(tert-butyldimethylsilyloxy)pentane(608136-22-7)

Safety Data

• Hazardous Substances Data: 608136-22-7(Hazardous Substances Data)

Upstream product

• 108-05-4 vinyl acetate 
• 608136-21-6 (+/-)-5-benzyloxy-1-tert-butyldimethylsilyloxy-2-pentanol 

Downstream Products

• 608136-29-4 C₂₆H₄₄N₂O₇Si 
• 608136-30-7 C₂₄H₄₂N₂O₆Si 
• 608136-31-8 3-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyridazine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 
• 608136-32-9 tetrahydro-pyridazine-1,2,3-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester 3-methyl ester 
• 173656-97-8 methyl (S)-1-benzyloxycarbonylhexahydropyridazine-3-carboxylate 

Relevant articles and documents

Lipase TL-mediated kinetic resolution of 5-benzyloxy-1-tert-butyldimethylsilyloxy-2-pentanol at low temperature: Concise asymmetric synthesis of both enantiomers of a piperazic acid derivative

Lipase TL-mediated kinetic resolution of (± )-5-benzyloxy-1-tert-butyldimethylsilyloxy-2-pentanol (5) at low temperature proceeded to give the corresponding (S)-alcohol 5 and (R)-acetate 6 in quantitative yields with high enantiomeric purity. The addition of bases such as pyridine, DMAP, 2,4- and 2,6-lutidines, or triethylamine considerably enhanced the rate of kinetic resolution. The alcohol (S)-5 and the acetate (R) -6 were converted to piperazic acid derivatives (R)- and (S)-3, respectively, via the intramolecular Mitsunobu reaction as a key step.