659-76-7

Basic information

• Product Name: 15-hydroxybimol.cyclic ester ;;
• CAS NO: 659-76-7
• Molecular Weight: 480.772
• Mol File: 659-76-7.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: 15-hydroxybimol.cyclic ester ;;(CAS DataBase Reference)
• NIST Chemistry Reference: 15-hydroxybimol.cyclic ester ;;(659-76-7)
• EPA Substance Registry System: 15-hydroxybimol.cyclic ester ;;(659-76-7)

Safety Data

• Hazardous Substances Data: 659-76-7(Hazardous Substances Data)

Upstream product

• 4617-33-8 15-hydroxylpentadecanoic acid 
• 76529-42-5 methyl 15-hydroxypentadecanoate 
• 71736-22-6 15-iodo-pentadecanoic acid 
• 93472-40-3 trimethylsilyl 15-(trimethylsiloxy)pentadecanoate 
• 109182-98-1 Acrylic acid 12-iodo-dodecyl ester 

Relevant articles and documents

Macrolactonization Reactions Driven by a Pentafluorobenzoyl Group**

Macrolactones constitute a privileged class of natural and synthetic products with a broad range of applications in the fine chemicals and pharmaceutical industry. Despite all the progress made towards their synthesis, notably from seco-acids, a macrolactonization promoter system that is effective, selective, flexible, readily available, and, insofar as possible, compatible with manifold functional groups is still lacking. Herein, we describe a strategy that relies on the formation of a mixed anhydride incorporating a pentafluorophenyl group which, due to its high electronic activation enables a convenient access to macrolactones, macrodiolides and esters with a broad versatility. Kinetic studies and DFT computations were performed to rationalize the reactivity of the pentafluorophenyl group in macrolactonization reactions.

Efficient method for the lactonization of ω-hydroxycarboxylic acids with di-2-thienyl carbonate by the promotion of catalytic amounts of DMAP and Hf(OTf)4

An efficient method for the synthesis of macrolides from ω-hydroxycarboxylic acids is established by using an equimolar amount of di-2-thienyl carbonate (2-DTC) and catalytic amounts of 4-(dimethylamino) pyridine (DMAP) and group 4 metal triflates such as hafnium(IV) trifluoromethanesulfonate (Hf(OTf)4). Copyright

An effective method for the synthesis of carboxylic esters and lactones using substituted benzoic anhydrides with Lewis acid catalysts

An efficient mixed-anhydride method for the synthesis of carboxylic esters and lactones using benzoic anhydride having electron withdrawing substituent(s) is developed by the promotion of Lewis acid catalysts. In the presence of a catalytic amount of TiCl2(ClO4)2, various carboxylic esters are prepared in high yields through the formation of the corresponding mixed-anhydrides from 3,5-bis(trifluoromethyl)benzoic anhydride and carboxylic acids. The combined catalyst consisting of TiCl 2(ClO4)2 together with chlorotrimethylsilane functions as an effective catalyst for the synthesis of carboxylic esters from free carboxylic acids and alcohols with 4-(trifluoromethyl)benzoic anhydride. Various macrolactones are prepared from the free ω-hydroxycarboxylic acids by the combined use of 4-(trifluoromethyl)benzoic anhydride and titanium(IV) catalysts together with chlorotrimethylsilane under mild reaction conditions. The lactonization of trimethylsilyl ω-(trimethylsiloxy) carboxylates using 4-(trifluoromethyl)benzoic anhydride is also promoted at room temperature in the presence of a catalytic amount of TiCl 2(ClO4)2. An 8-membered ring lactone, a synthetic intermediate of cephalosporolide D, is successfully synthesized according to this mixed-anhydride method using 4-(trifluoromethyl)benzoic anhydride by the promotion of a catalytic amount of Hf(OTf)4.