874461-82-2

Upstream product

• 20445-33-4 (R)-methoxytrifluoromethylphenylacetyl chloride 
• 74985-25-4 (+)-((2S,3R)-3-decyloxiran-2-yl)methanol 
• 74962-99-5 (Z)-tridec-2-en-1-ols 
• 51887-25-3 tridec-2-yn-1-ol 
• 39637-99-5 (S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride 

Relevant academic research and scientific papers

Synthesis of disparlure analogues, using resolution on microcrystalline cellulose triacetate-I

The gypsy moth, Lymantria dispar, uses a chiral epoxide, (+)-(7R,8S)-2-methyl-7,8-epoxyoctadecane, (+)-disparlure, as its main sex attractant. The moths can detect both enantiomers of disparlure and respond differently to each one. In an effort to understand the structure-activity relationships of the gypsy moth olfactory system, we prepared the analogues of (+)- and (-)-disparlure. The key intermediate in route to the analogues was 2-epoxytridecan-1-ol. Herein we report the resolution of 2-epoxytridecan-1-yl esters on microcrystalline cellulose triacetate and the synthesis of 5-oxa and (5Z)-ene analogues of (+)- and (-)-disparlure. An effort to make 5-aza analogues resulted in the formation of anti-5-(1-hydroxy-1-undecyl)-3-(3-methylbutyl) oxazolidin-2-one. The analogues were tested for their electroantennogram responses and for their ability to bind to pheromone-binding protein 1 (PBP1). We found that the 5-oxa analogues gave strong responses and that the antenna and the PBP1 no longer distinguish the enantiomers of the 5-oxa analogues. The analogues all bound the PBP1 with similar affinity to (-)-disparlure.

Tritium-Labeled Enantiomers of Disparlure. Synthesis and in Vitro Metabolism

Both of the enantiomers of disparlure, the gypsy moth sex attractant, have been prepared at high specific activity (58 Ci/mmol) by homogeneous tritiation of the optically active alkenyl oxiranes.An improved preparation of the racemic disparlure is also described.The radiolabeled epoxides are cleanly converted to a single product by enzymes isolated from adult gypsy moths (Lymantria dispar).Enzymatic activity obtained from male antennae showed the highest conversion; enzymes isolated from female antennae and from male and female legs showed lower activity.The identification of the metabolite as the threo-7,8-diol is established by independent synthesis and by chemical derivatizations to the diacetate, n-butylboronate, and bis(trimethylsilyl) ether.A symmetrical epoxide analogous to disparlure is converted to a diol product at a significantly lower rate.