(R)-(-)-jasmine lactone

Base Information

• Chemical Name: (R)-(-)-jasmine lactone
• CAS No.: 136173-93-8
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.236
• Mol file: 136173-93-8.mol

Synonyms:

Chemical Property of (R)-(-)-jasmine lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(-)-jasmine lactone

There total 12 articles about (R)-(-)-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: 76.0%

methyl (R,Z)-5-hydroxydec-7-enoate → (R)-(-)-jasmine lactone (136173-93-8,68170-58-1)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 0 - 20 ℃; for 6h;

Reference yield: 60.0%

(+)-(6R)-Tetrahydro-6-(pent-2-ynyl)-2H-pyran-2-one (136173-92-7) → (R)-(-)-jasmine lactone (136173-93-8,68170-58-1)

Guidance literature:

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

DOI:10.1002/hlca.19910740412

Reference yield:

(-)-(5S)-<(tert-Butyl)diphenylsilyloxy>-5-hydroxyhexanoate d'ethyle (136113-69-4) → (R)-(-)-jasmine lactone (136173-93-8,68170-58-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / Et₃N / CH₂Cl₂ / 1) -5 deg C, 30 min., 2) r.t., 30 min.

2: 46 percent / Bu₄NF / silicagel / tetrahydrofuran

3: 1) BuLi, BF₃*Et₂O / 1) THF, -78 deg C, 2) THF, -78 deg C

4: KOH / aq. ethanol

5: Amberlyst 15 (H⁺), molecular sieves 4 Angstroem / acetonitrile / 4.5 h

6: 60 percent / H₂ / 5percent Pd / BaSO₄ / hexane; quinoline

With potassium hydroxide; n-butyllithium; 4 A molecular sieve; Amberlyst 15 (H⁺); boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; silica gel; triethylamine; Pd-BaSO₄; In tetrahydrofuran; quinoline; ethanol; hexane; dichloromethane; acetonitrile;

DOI:10.1002/hlca.19910740412

upstream raw materials:

(+)-(6R)-Tetrahydro-6-(pent-2-ynyl)-2H-pyran-2-one

Jasmin lactone

(-)-(5S)-<(tert-Butyl)diphenylsilyloxy>-5-hydroxyhexanoate d'ethyle

(-)-(5S)-6-<(tert-Butyl)diphenylsilyloxy>-5-(methanesulfonyloxy)hexanoate d'ethyle

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.