(6S)-(+)-jasmine lactone

Base Information

• Chemical Name: (6S)-(+)-jasmine lactone
• CAS No.: 136173-91-6
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.236
• Mol file: 136173-91-6.mol

Synonyms:

Chemical Property of (6S)-(+)-jasmine lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S)-(+)-jasmine lactone

There total 13 articles about (6S)-(+)-jasmine lactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

(-)-(6S)-Tetrahydro-6-(pent-2-ynyl)-2H-pyran-2-one (136173-90-5) → (6S)-(+)-jasmine lactone (136173-91-6,68170-58-1)

Guidance literature:

With hydrogen; Pd-BaSO₄; In quinoline; hexane;

DOI:10.1002/hlca.19910740412

Reference yield: 38.0%

(6S)-6-(2-pentynyl)-5,6-dihydro-2H-2-pyranone (916667-94-2) → (6S)-(+)-jasmine lactone (136173-91-6,68170-58-1)

Guidance literature:

With quinoline; Lindlar's catalyst; hydrogen; In ethyl acetate; for 12h;

DOI:10.1016/j.tetlet.2006.08.135

Reference yield:

(-)-(5S)-5,6-Epoxyhexanoate d'ethyle (133634-37-4) → (6S)-(+)-jasmine lactone (136173-91-6,68170-58-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) BuLi, BF₃*Et₂O / 1) THF, -78 deg C, 10 min., 2) THF, -78 deg C, 30 min.

2: 84 percent / H₂ / 5percent Pd / BaSO₄ / hexane; quinoline

With n-butyllithium; boron trifluoride diethyl etherate; hydrogen; Pd-BaSO₄; In quinoline; hexane;

DOI:10.1002/hlca.19910740412

upstream raw materials:

(-)-(6S)-Tetrahydro-6-(pent-2-ynyl)-2H-pyran-2-one

(6S)-6-(2-pentynyl)-5,6-dihydro-2H-2-pyranone

3-(tert-butyl-dimethyl-silanyloxy)-oct-5-ynal

3-(tert-butyl-dimethyl-silanyloxy)-oct-5-yn-1-ol

Refernces

• 1、 Nohira, Hiroyuki,Mizuguchi, Keiko,Murata, Toru,Yazaki, Yuko,Kanazawa, Miho,Aoki, Yoshio,Nohira, Misako. "Optical resolution of fragrant lactones". . p. 1359 - 1370. Retrieved 2007/10/03.