65184-36-3

Upstream product

• 112-29-8 1-bromo dodecane 
• 23788-74-1 (R)-2,2-dimethyl-1,3-dioxolane-4-ylmethyl p-toluenesulfonate 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 

Downstream Products

• 755015-88-4 (S)-4-dichloromethyl-2,2-dimethyl-4-undecyl-1,3-dioxolane 
• 129752-93-8 Toluene-4-sulfonic acid (S)-2-hydroxy-tridecyl ester 
• 1713-31-1 (S)-(-)-1,2-epoxytridecane 
• 755016-02-5 (R)-6-(t-butyldiphenylsiloxymethyl)-6-undecyltetrahydropyran-2-one 
• 755016-01-4 (R)-6-(t-butyldiphenylsiloxymethyl)heptadec-1-en-6-ol 
• 755015-98-6 (S)-1-(t-butyldiphenylsilyloxy)-2-chloromethyl-2-tridecanol 
• 755015-99-7 (R)-2-t-butyldiphenylsilyloxymethyl-2-undecyloxirane 
• 755015-95-3 (S)-4-chloromethyl-2,2-dimethyl-4-undecyl-1,3-dioxolane 

Relevant academic research and scientific papers

Asymmetric synthesis of 5-hexadecanolide, pheromone of the queen of the Oriental hornet, Vespa orientalis

An efficient asymmetric synthesis of 5-hexadecanolide from a chiral epoxide is described. Both the enantiomeric forms of the chiral epoxide are easily available from mannitol and ascorbic acid. The key step in the synthesis is the formation of δ-lactone from δ-hydroxy acetal using m-CPBA and BF3-OEt2.

A simple synthesis of the queen substance of oriental hornet, Vespa orientalis from (R)-2,3-O-isopropylideneglycerol

(R)- and (S)-5-Hexadecanolides I have been synthesized in high optical purity using (R)-2,3-O-isopropylideneglycerol 1 as the chiral source.Stereoisomerization of 1,2-diol 3, Grignard coupling, regioselective Grignard reaction and oxidative cleavage of olefin are some of the key steps involved in it.