162490-18-8

Basic information

• Product Name: (3R,4R)-tert-Butyl 3--5-((tert-butyldimethylsilyl)oxy)-4-methylpentanoate
• Synonyms: (3R,4R)-tert-Butyl 3--5-((tert-butyldimethylsilyl)oxy)-4-methylpentanoate
• CAS NO: 162490-18-8
• Molecular Weight: 511.82
• Mol File: 162490-18-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3R,4R)-tert-Butyl 3--5-((tert-butyldimethylsilyl)oxy)-4-methylpentanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R)-tert-Butyl 3--5-((tert-butyldimethylsilyl)oxy)-4-methylpentanoate(162490-18-8)
• EPA Substance Registry System: (3R,4R)-tert-Butyl 3--5-((tert-butyldimethylsilyl)oxy)-4-methylpentanoate(162490-18-8)

Safety Data

• Hazardous Substances Data: 162490-18-8(Hazardous Substances Data)

Upstream product

• 17480-69-2 (S)-N-benzyl-1-phenylethylamine 
• 138877-99-3 (R)-(E)-tert-Butyl 5-(tert-Butyldimethylsiloxy)-4-methyl-2-pentenoate 
• 104701-87-3 (2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal 
• 93454-85-4 (S)-3-(tert-butyldimethylsilyloxy)-2-methylpropionic acid methyl ester 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Relevant articles and documents

A three component coupling approach to a chiral 1β-methylcarbapenem key intermediate

Conjugate addition of N-benzyl-N-((R)-1-phenylethyl)amine (R)-5 to (R)-(E)-tert-butyl 5-((tert-butyldimethylsilyl)oxy)-4-methyl-2-pentenoate (10a) produced the (3S,4R)-syn-adduct 14 with essentially 100% de in 84% yield, whereas the addition of (S)-5 to 10a afforded the (3R,4R)-antiadduct 15 with essentially 100% de in 95% yield. The syn adduct 14 was converted upon sequential treatment with lithium diisopropylamide-methylaluminum dichloride-acetaldehyde to the key intermediate 21; the diastereoisomer ratio of 21 to other diastereoisomers was 80:20. Conversion of 21 to a 1β-methylcarbapenem key intermediate 26 was carried out readily according to the known procedures.