150822-79-0Relevant academic research and scientific papers
Method for synthesizing sex pheromone of hyphantria cunea
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Paragraph 0059-0062, (2021/04/17)
The invention relates to the technical field of hyphantria cunea prevention and treatment, in particular to a synthetic method for synthesizing sex pheromone of hyphantria cunea. According to a traditional method for synthesizing (3Z,6Z,9S,10R)-9,10-epoxy-3,6-heneicosadiene by using propargyl alcohol as a starting material in the traditional technology, various side reactions are liable to occur during a sulfonic acid esterification reaction on a key intermediate (2S,3R)-2,3-epoxy-1-tetradecanol by using trifluoromethanesulfonic anhydride. In order to solve the problems, the (3Z,6Z,9S,10R)-9,10-epoxy-3,6-heneicosadiene is successfully synthesized by taking propargyl alcohol as an initial raw material and taking a Sharpless asymmetric dihydroxylation reaction as a key step without the step of the sulfonic acid esterification reaction on a key intermediate (2S,3R)-2,3-epoxy-1-tetradecanol by trifluoromethanesulfonic anhydride in the preparation process. Therefore, the whole reaction is mild and controllable and few in side reactions, and enantioselectivity is high.
Method for synthesizing (3Z,6Z,9S,10R)-9,10-epoxy-3,6-heneicosadiene
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, (2021/06/23)
The invention belongs to the technical field of green pesticides, and discloses a novel method for synthesizing a main active component (3Z,6Z,9S,10R)-9,10-epoxy-3,6-heneicosadiene of sex pheromone of fall webworms. The method comprises the steps: by taki
Concise total synthesis of (3Z,6Z,9S,10R)-9,10-epoxy-1,3,6-heneicosatriene, sex pheromone component of Hyphantria Cunea
Che, Chao,Zhang, Zhong-Ning
, p. 2187 - 2193 (2007/10/03)
The total synthesis of (3Z,6Z,9S,10R)-9,10-epoxy-1,3,6-heneicosatriene, sex pheromone component of Hyphantria cunea, using a convergent synthetic strategy, was achieved through the regioselective coupling of the two fragments, chiral epoxy tosylate and 1,
A simple synthetic method for chiral 1,2-epoxides and the total synthesis of a chiral pheromone epoxide
Zhang, Zhi-Bo,Wang, Zhi-Min,Wang, Yu-Xiu,Liu, Huan-Quan,Lei, Gui-Xin,Shi, Min
, p. 53 - 58 (2007/10/03)
Chiral 1,2-epoxyalkan-3-ol tosyl esters 4a-h were successfully synthesized from alkynols or allyl chlorides in three steps using Sharpless AD reaction as a key step in good yields. The chiral insect pheromone epoxide (6Z,9S,10R)-9,10-epoxyhenicos-6-ene 9 was thus smoothly synthesized from the corresponding key intermediate 4g.
A facile synthetic method for chiral 1,2-epoxides and the total synthesis of chiral pheromone epoxides
Zhang, Zhi-Bo,Wang, Zhi-Min,Wang, Yu-Xiu,Liu, Huan-Quan,Lei, Gui-Xin,Shi, Min
, p. 837 - 840 (2007/10/03)
Chiral 1,2-epoxy-3-alkanol tosylates were successfully synthesized from alkynols in three steps using the Sharpless AD reaction as a key step in good yields. Two chiral insect pheromone epoxides were smoothly obtained from the corresponding key intermediate.
Total synthesis of enantiomers of (3Z,6Z)-cis-9,10-epoxy 1,3,6- henicosatriene - The pheromonal component of Diacrisia obliqua
Yadav,Valli, Madabhushi Y.,Prasad
, p. 7551 - 7562 (2007/10/03)
Synthesis of enantiomers of (3Z,6Z)-cis-9,10-epoxy 1,3,6- henicosatriene, the pheromonal component of Diacrisia obliqua was achieved through alkylative epoxide rearrangement and stereoselective Wittig olefination reactions as the key steps.
Access to unsaturated chiral epoxides. Part II. Synthesis of a component of the sex pheromone of Phragmatobia fuliginosa
Soulie,Boyer,Lallemand
, p. 625 - 636 (2007/10/02)
A general method for the synthesis of chiral cis-epoxides substituted bearing a saturated chain and an unsaturated chain is described. This method is used to synthesize both enantiomers of compound 1.
Alkylative Epoxide Rearrangement. A Stereospecific Approach to Chiral Epoxide Pheromones
Bell, Thomas W.,Ciaccio, James A.
, p. 5153 - 5162 (2007/10/02)
The alkylative rearrangement of 1,2-epoxy-3-alkanol tosylates is applied to the synthesis of chiral epoxide pheromones.Attack at the terminal carbon atom of epoxy tosylates by lithioacetylenes and cyclization of the intermediate tosyloxy alcohols produces
ALKYLATIVE EPOXIDE REARRANGEMENT. APPLICATION TO STEREOSELECTIVE SYNTHESIS OF CHIRAL PHEROMONE EPOXIDES.
Bell, Thomas W.,Claccio, James A.
, p. 865 - 868 (2007/10/02)
An approach is described for the stereospecific conversion of threo and erythro 1,2-epoxy-3-alkanol tosylates to cis and trans internal epoxides, respectively.The method is illustrated by the synthesis of chiral epoxides, including insect pheromones.
