1331869-16-9

Basic information

• Product Name: (R)-N,N-diallyl-5-(benzyloxy)-3-hydroxypentanethioamide
• Synonyms: (R)-N,N-diallyl-5-(benzyloxy)-3-hydroxypentanethioamide
• CAS NO: 1331869-16-9
• Molecular Weight: 319.468
• Mol File: 1331869-16-9.mol

Chemical Properties

• CAS DataBase Reference: (R)-N,N-diallyl-5-(benzyloxy)-3-hydroxypentanethioamide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N,N-diallyl-5-(benzyloxy)-3-hydroxypentanethioamide(1331869-16-9)
• EPA Substance Registry System: (R)-N,N-diallyl-5-(benzyloxy)-3-hydroxypentanethioamide(1331869-16-9)

Safety Data

• Hazardous Substances Data: 1331869-16-9(Hazardous Substances Data)

Upstream product

• 6296-61-3 N,N-diallylacetamide 
• 1182707-33-0 N,N-diallylmethylmethanethioamide 
• 19790-60-4 3-Benzyloxypropanal 

Downstream Products

• 1331869-20-5 (R)-tert-butyl 7-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-3-oxoheptanoate 
• 1331869-21-6 tert-butyl 2-((4R,6R)-6-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate 
• 1331869-22-7 tert-butyl 2-((4R,6R)-2,2-dimethyl-6-(2-(tosyloxy)ethyl)-1,3-dioxan-4-yl)acetate 
• 125971-86-0 tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate 
• 134395-00-9 (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester 
• 125971-95-1 tert-butyl (4R,6R)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate 
• 134523-00-5 atorvastatin 
• 1347738-07-1 (R)-N,N-diallyl-5-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)pentanethioamide 

Relevant articles and documents

THIOAMIDE COMPOUND, METHOD FOR PRODUCING THIOAMIDE COMPOUND, METHOD FOR PRODUCING [(4R,6R)-6-AMINOETHYL-1,3-DIOXANE-4-YL]ACETATE DERIVATIVE, AND METHOD FOR PRODUCING ATORVASTATIN

A thioamide compound represented by the following general formula (1): wherein, in the general formula (1), R1 represents one of -OR11 and -NR12R13; R2 and R3 each independently represent one of a protecting group of an amide group and a hydrogen atom; the R11 represents one of a protecting group of a hydroxyl group and a hydrogen atom; and the R12 and R13 each independently represent one of a protecting group of an amino group and a hydrogen atom, where the R12 and R13 may together form a protecting group having a cyclic structure.

A simplified catalytic system for direct catalytic asymmetric aldol reaction of thioamides; Application to an enantioselective synthesis of atorvastatin

A new catalytic system was developed for the direct catalytic asymmetric aldol reaction of thioamides. The new lithium-free Cu catalyst (second-generation catalyst) exhibited enhanced catalytic efficiency over the previously developed catalyst comprising [Cu(CH3CN) 4]PF6/Ph-BPE/LiOAr (first-generation catalyst), which required a tedious catalyst preparation process. In the reaction with the second-generation catalyst, the intermediate Cu-aldolate functioned as a Bronsted base to generate thioamide enolate, efficiently driving the catalytic cycle. The present aldol methodology culminated in a concise asymmetric synthesis of atorvastatin (Lipitor: atorvastatin calcium), a widely prescribed HMG-CoA reductase inhibitor for lowering low-density lipoprotein cholesterol.