58701-06-7

Upstream product

• 65370-61-8 trans-6-cis-11-hexadecadien-1-ol 
• 65115-50-6 11-(2-tetrahydropyranyloxy)-5E-undecenal 
• 37935-47-0 2-(5-bromopentyloxy)tetrahydropyran 
• 928-90-5 5-hexyl-1-ol 
• 87291-73-4 11-(2-tetrahydropyranyloxy)-5-undecyn-1-ol 
• 87291-74-5 11-(2-tetrahydropyranyloxy)-5E-undecen-1-ol 
• 110-87-2 3,4-dihydro-2H-pyran 
• 37011-86-2 tetrahydro-2-(6-heptynyloxy)-2H-pyran 
• 93092-34-3 (Z)-11-hexadecen-6-yn-1-ol 
• 65370-59-4 (Z)-1-(tetrahydropyran-2-yloxy)-11-hexadecen-6-yne 
• 104837-04-9 (E)-11-hexadecen-6-yn-1-ol 
• 142-68-7 TETRAHYDROPYRANE 
• 110-53-2 1-Bromopentane 
• 34626-51-2 5-bromopentan-1-ol 

Relevant academic research and scientific papers

Pheromones: 87. An efficient synthesis of (6E,11Z)-6,11-hexadecadienyl acetate and (6E,11Z)-6,11-hexadecadienal: Female sex pheromone components of Antheraea pernyi and A. polyphemus (Lepidoptera: Saturniidae)

(6E,11Z)-Hexadecadienyl acetate (15) and the corresponding aldehyde 16, the female sex pheromone components of Antheraea pernyi and A. polyphemus (Lepidoptera; Saturniidae) have been synthesized in 32% and 27% overall yields, respectively, and in 99% isomeric purity. Tetrahydropyran (1) was used as the starting material to obtain 5-bromopentanol (3) which was subsequently chain elongated to 7-(tetrahydropyran-2-yloxy)-1-heptyne (5) by the standard procedures. The organolithium compound from 5 was coupled with (Z)-1-bromo-4-nonene (11), obtained from the Wittig reaction between pentyltriphenylphosphonium bromide (9) and 4-(tetrahydropyran-2-yloxy)butanal (8) followed by bromination. The product, (Z)-1-(tetrahydropyran-2-yloxy)-11-hexadecen-6-yne (12) which resulted, was reduced with sodium/liquid ammonia to give 13 with the E-6 bond. Removal of the protecting group resulted in the desired alcohol 14 which on acetylation and oxidation gave the desired acetate 15 and the aldehyde 16, respectively.

SYNTHETIC INVESTIGATIONS IN THE FIELD OF INSECTS ATTRACTANTS (SEX ATTRACTANTS). XIV. STEREOSELECTIVE SYNTHESIS OF THE FOUR ISOMERS OF 6,11-HEXADECADIEN-1-OL AND THEIR ACETATES AND ALDEHYDES - COMPONENTS OF THE SEX PHEROMONES OF INSECTS OF THE FAMILY SATURNIIDAE (LEPIDOPTERA)

The four isomers of 6,11-hexadecadien-1-ol, their acetates, and the corresponding aldehydes were obtained by a common scheme based on the alkylation of 5-hexyn-1-ol by the tetrahydropyranyl ether of 1,5-pentamethylene bromohydrin, stereoselective reduction of the triple bond in the alkylation product 11-(2-tetrahydropyranyloxy)-5-undecyn-1-ol, oxidation of the obtained Z or E isomer of 11-(2-tetrahydropyranyloxy)-5-undecen-1-ol to the aldehyde, and stereoselective olefination of the latter with pentylidenetriphenylphosphorane under the conditions of the formation of a doubl e bond with a specific (Z or E) configuration of the substituents.Subsequent removal of the tetrahydropyranyl protection of the alcohol group in the Wittig reaction products by acid hydrolysis gave 6,11-hexadecadien-1-ols, the acetylation or oxidation of which led to the corresponding acetates or aldehydes.The latter are components of the sex pheromones of insects of the Saturniidae family.

Stereospecific Synthesis of (6E,11Z)-6,11-Hexadecadien-1-yl Acetate and (6E,11Z)-6,11-hexadecadien-1-al, the Sex Pheromone Components of Wild Silkmoth, Antheraea polyphemus

4-Pentynol (1) on alkylation with (Z)-4-nonenyl bromide (3) in the presence of base gives the enyne alcohol (4).The corresponding bromide (5) on two-carbon homologation with dimethyl malonate results into C16 enyne ester (6).This on conversion to alcohol (7) followed by stereospecific trans reduction of the acetylene function affords 8. 8 on acetylation gives the pheromone (9) while its oxidation affords another component, the pheromone (10).