(-)-Bakkenolide E

Base Information

Chemical Name:(-)-Bakkenolide E
CAS No.:21807-96-5
Molecular Formula:C₂₂H₃₀O₆
Molecular Weight:390.477
Hs Code.:
Mol file:21807-96-5.mol

Synonyms:2-Butenoicacid, 2-methyl-,3'-(acetyloxy)decahydro-7',7'a-dimethyl-4-methylene-2-oxospiro[furan-3(2H),2'-[2H]inden]-4'-ylester, [2'R-[2'a,3'a,3'aa,4'b(E),7'a,7'aa]]-; Crotonic acid, 2-methyl-, 7'-ester with3'a,4,4',5,5',6',7',7'ab-octahydro-1'b,7'a-dihydroxy-3'ab,4'b-dimethyl-4-methylenespiro[furan-3(2H),2'-indan]-2-oneacetate, (E)- (8CI); Spiro[furan-3(2H),2'-[2H]inden], 2-butenoic acid deriv.;Spiro[furan-3(2H),2'-indan]-2-one, 3'a,4,4',5,5',6',7',7'ab-octahydro-1'b,7'a-dihydroxy-3'ab,4'b-dimethyl-4-methylene-, 1'-acetate 2-methylcrotonate (8CI);(-)-Bakkenolide E; Bakkenolide E

Suppliers and Price of (-)-Bakkenolide E

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 2 raw suppliers

Chemical Property of (-)-Bakkenolide E

Chemical Property:

Purity/Quality:: 99% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (-)-Bakkenolide E

There total 24 articles about (-)-Bakkenolide E 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: 86.0%

: 18456-00-3
(-)-Bakkenolide C

: 108-24-7
acetic anhydride

: 18455-98-6,19903-88-9,21807-96-5,31728-56-0
bakkenolide B

Guidance literature:: With pyridine; dmap;
DOI:10.1002/1521-3773(20001201)39:23<4314::AID-ANIE4314>3.0.CO;2-Q

Reference yield:

: 192197-73-2
(1S,2R,6S,8S)-ethyl-1,2-dimethyl-7-oxobicyclo[4.3.0]nonane-8-carboxylate

: 18455-98-6,19903-88-9,21807-96-5,31728-56-0
bakkenolide B

Guidance literature:: Multi-step reaction with 10 steps

1.1: toluene / Heating

2.1: Mn(O₂CCH₃)3 / ethanol / 20 °C

3.1: NaHMDS / tetrahydrofuran / 4 h / -65 °C

3.2: C₆H₅SeBr / tetrahydrofuran / -65 - 0 °C

3.3: 77 percent / aq. H₂O₂; AcOH / 1.5 h / 0 °C

4.1: NaBH₄; CeCl₃ / ethanol / 1.5 h / -30 °C

5.1: 57 percent / vanadyl acetylacetonate; TBHP / toluene; 1,2-dichloro-ethane / 6 h / 50 - 60 °C

6.1: 83 percent / (ClCO)2; DMSO; Et₃N / CH₂Cl₂ / -60 - -20 °C

7.1: 83 percent / SmI₂ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

8.1: 82 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

9.1: 86 percent / toluene / 32 h / Heating

10.1: 86 percent / pyridine; DMAP / 2 h / 20 °C

With pyridine; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; samarium diiodide; cerium(III) chloride; oxalyl dichloride; vanadyl acetylacetonate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; manganese triacetate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; 1,2-dichloro-ethane; toluene; 4.1: Luche reduction;
DOI:10.1021/ja0208456

Reference yield:

: 322479-98-1
(-)-1,10-didehydro-7-epi-9-oxo-bakkenolide A

: 18455-98-6,19903-88-9,21807-96-5,31728-56-0
bakkenolide B

Guidance literature:: Multi-step reaction with 7 steps

1: NaBH₄; CeCl₃ / ethanol / 1.5 h / -30 °C

2: 57 percent / vanadyl acetylacetonate; TBHP / toluene; 1,2-dichloro-ethane / 6 h / 50 - 60 °C

3: 83 percent / (ClCO)2; DMSO; Et₃N / CH₂Cl₂ / -60 - -20 °C

4: 83 percent / SmI₂ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

5: 82 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

6: 86 percent / toluene / 32 h / Heating

7: 86 percent / pyridine; DMAP / 2 h / 20 °C

With pyridine; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; samarium diiodide; cerium(III) chloride; oxalyl dichloride; vanadyl acetylacetonate; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; 1,2-dichloro-ethane; toluene; 1: Luche reduction;
DOI:10.1021/ja0208456