(3R,6S,7R)-cucurbic acid

Base Information

• Chemical Name: (3R,6S,7R)-cucurbic acid
• CAS No.: 146143-02-4
• Molecular Formula: C₁₂H₂₀O₃
• Molecular Weight: 212.289
• Mol file: 146143-02-4.mol

Synonyms:(3R,6S,7R)-cucurbic acid

Chemical Property of (3R,6S,7R)-cucurbic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,6S,7R)-cucurbic acid

There total 45 articles about (3R,6S,7R)-cucurbic acid 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:

jasmonic acid (6894-38-8) → (+)-6-epi-7-iso-cucurbic acid (120330-52-1) + (3R,6S,7R)-cucurbic acid (146143-02-4)

Guidance literature:

With sodium tetrahydroborate; In methanol;

DOI:10.1016/0031-9422(91)85038-2

Reference yield:

(1S,5S,8R)-8-<(2'Z)-pent-2'-enyl>-2-oxybicyclo<3.2.1>octan-3-on (128820-28-0,807630-26-8) → [(1S,2R,3S)-3-Hydroxy-2-((Z)-pent-2-enyl)-cyclopentyl]-acetic acid (34027-33-3,53369-27-0,54595-06-1,54595-07-2,54595-08-3,54595-09-4,58240-50-9,109008-59-5,117179-84-7,120330-52-1,131488-83-0,139560-28-4,143234-96-2,143234-98-4,146143-02-4)

Guidance literature:

With potassium hydroxide; water; In methanol; at 20 ℃; for 2h;

DOI:10.1080/00397919708004999

Reference yield:

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one (39746-01-5) → [(1S,2R,3S)-3-Hydroxy-2-((Z)-pent-2-enyl)-cyclopentyl]-acetic acid (34027-33-3,53369-27-0,54595-06-1,54595-07-2,54595-08-3,54595-09-4,58240-50-9,109008-59-5,117179-84-7,120330-52-1,131488-83-0,139560-28-4,143234-96-2,143234-98-4,146143-02-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 98 percent / benzene / 0.5 h / 20 °C

2: 71 percent / DBU / CH₂Cl₂ / 3 h / 20 °C

3: 90 percent / H₂ / Rh-Al₂O₃ / ethanol / 760 Torr

4: 98 percent / NaOH; water / methanol / 3 h / 20 °C

5: 70 percent / iodobenzene diacetate; iodine / benzene / 12.75 h / Heating; two 100W tungsten filament lamps

6: NaIO₄ / RuCl₃*H₂O / acetonitrile; CCl₄; H₂O / 12 h

7: 426 mg / benzene; methanol; hexane / 0.5 h / 20 °C

8: 410 mg / DIBAL-H / tetrahydrofuran / 3 h / -78 °C

9: 240 mg / KN(TMS)2 / tetrahydrofuran / -78 - 0 °C

10: KOH; water / methanol / 2 h / 20 °C

With potassium hydroxide; sodium hydroxide; sodium periodate; [bis(acetoxy)iodo]benzene; water; hydrogen; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; ruthenium trichloride; rhodium on alumina; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; hexane; dichloromethane; water; acetonitrile; benzene; 1: Wittig reaction / 2: Elimination / 3: Catalytic hydrogenation / 4: Hydrolysis / 5: oxidative decarboxylation / 6: Catalytic oxidation / 7: Methylation / 8: Reduction / 9: Wittig reaction / 10: Hydrolysis;

DOI:10.1080/00397919708004999

upstream raw materials:

n-propyltriphenylphosphonium bromide

((3aR,4S,6aS)-2-Hydroxy-hexahydro-cyclopenta[b]furan-4-yl)-acetic acid

cis-bicyclo<4.3.0>nona-3,7-diene

[(1R,2S)-2-(2-Oxo-ethyl)-cyclopent-3-enyl]-acetaldehyde

Downstream raw materials:

(+/-)-methyl dihydroepijasmonate

(+/-)-methyl trans-dihydrojasmonate

methyl (2-(2-pent-2Z-enyl)-3-oxocyclopentyl)acetate

(+/-)-Cucurbic acid