136173-93-8

Upstream product

• 136173-92-7 (+)-(6R)-Tetrahydro-6-(pent-2-ynyl)-2H-pyran-2-one 
• 25524-95-2 Jasmin lactone 
• 928-96-1 (Z)-3-Hexen-1-ol 
• 6789-80-6 (3Z)-hexenal 
• 136113-72-9 (5R)-5-Hydroxydec-7-ynoate d'ethyle 
• 87086-56-4 (R)-5-Hydroxy-dec-7-ynoic acid 
• 136113-71-8 (+)-(5R)-5,6-Epoxyhexanoate d'ethyle 
• 133634-34-1 (-)-(5S)-5,6-Dihydroxyhexanoate d'ethyle 
• 136113-70-7 (-)-(5S)-6-<(tert-Butyl)diphenylsilyloxy>-5-(methanesulfonyloxy)hexanoate d'ethyle 
• 136113-69-4 (-)-(5S)-<(tert-Butyl)diphenylsilyloxy>-5-hydroxyhexanoate d'ethyle 

Relevant academic research and scientific papers

Method for asymmetric synthesis of (R)-jasmine lactone

The invention discloses a method for asymmetric synthesis of (R)-jasmine lactone. The method comprises the steps: oxidating (Z)-3-hexen-1-ol 1, which serves as a starting raw material, with a DMP reagent, so as to obtain (Z)-3-hexenoic aldehyde 2; then, carrying out an asymmetric addition reaction with methyl alkyne-butyrate in the presence of a (R,R)-ProPhenol ligand and zinc methyl, so as to obtain (S,Z)-5-hydroxyl-7-decen-3-methyl acetylenate 3; reducing a triple bond into a single bond with NaBH4 in the presence of CuI, so as to produce (R,Z)-5-hydroxyl-7-methyl decenoate 4; and finally, carrying out treatment with para-toluenesulfonic acid, and carrying out ring closing, thereby obtaining the target product, i.e., (R)-jasmine lactone. According to the method, the synthesis route is simple and direct, the reaction conditions are mild, the total yield is 42%, and the optical purity of the product is 95%.

Optical resolution of fragrant lactones

Optical resolution of six chiral fragrant lactones (δ-jasmine lactone, massoia lactone, tuberolactone, pentynyllactone, δ-decalactone, and γ- nonalactone) was investigated by means of either the diastereomeric salt formation method or the diastereomeric amide formation method. Using these procedures, we obtained each enantiomer from five of the six lactones, except for massoia lactone. All five lactones were obtained in a good yield and with high optical purity. Sensoric characteristics on both enantiomers and racemic modification of four lactones are given.

Synthesis of (-)-(6R)- and (+)-(6S)-Tetrahydro-6--2H-pyran-2-one, lactones from Jasminum grandiflorum L. and from Polianthes tuberosa L.

(-)-(2S)-Ethyl 2-hydroxyhexanedioate ((2S)-2) was obtained by kinetic resolution of racemic ethyl 2-hydroxyhexanedioate with baker's yeast.The key intermediates (+)-(5R)- and (-)-(5S)-ethyl 5,6-epoxyhexanoate ((5R)- and (5S)-6, resp.) are proved to be use