1-Cyclohexene-1-aceticacid,3-hydroxy-6-oxo-4-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]-,methyl ester, (3R,4R)- (9CI)

Base Information

• Chemical Name: 1-Cyclohexene-1-aceticacid,3-hydroxy-6-oxo-4-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]-,methyl ester, (3R,4R)- (9CI)
• CAS No.: 152340-70-0
• Molecular Formula: C29H44 O4
• Molecular Weight: 456.666
• Mol file: 152340-70-0.mol

Synonyms:1-Cyclohexene-1-aceticacid, 3-hydroxy-6-oxo-4-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-,methyl ester, [3R-[3a,4a(2E,6E,10E)]]-; Eunicenone A

Chemical Property of 1-Cyclohexene-1-aceticacid,3-hydroxy-6-oxo-4-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]-,methyl ester, (3R,4R)- (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Cyclohexene-1-aceticacid,3-hydroxy-6-oxo-4-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]-,methyl ester, (3R,4R)- (9CI)

There total 16 articles about 1-Cyclohexene-1-aceticacid,3-hydroxy-6-oxo-4-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]-,methyl ester, (3R,4R)- (9CI) 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: 98.0%

[(7S,10R,11R)-10-Hydroxy-11-((2E,6E,10E)-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenyl)-6,14-dioxa-dispiro[4.1.5.2]tetradec-8-en-8-yl]-acetic acid methyl ester (332343-91-6) → eunicenone A (152340-70-0)

Guidance literature:

With sodium periodate; camphor-10-sulfonic acid; In methanol; water; at 23 ℃; for 7h;

DOI:10.1021/ja004043r

Reference yield:

Geranylgeraniol (24034-73-9) → eunicenone A (152340-70-0)

Guidance literature:

Multi-step reaction with 16 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

1.2: tetrahydrofuran; hexane / 1.5 h / -78 °C

2.1: CuCN / tetrahydrofuran / 1 h / -40 - 0 °C

2.2: 427 mg / tetrahydrofuran; hexane / 12 h / 0 °C

3.1: Cp₂ZrHCl / tetrahydrofuran / 0.75 h / 20 °C

3.2: 75 percent / ZnCl₂ / Pd(PPh₃)4 / tetrahydrofuran / 1 h / 20 °C

4.1: DIBAL-H / tetrahydrofuran; toluene / 0.67 h / -78 - 0 °C

4.2: MeOH; Na₂SO₄*10H₂O / tetrahydrofuran / 0.5 h / 23 °C

5.1: pyridine; 4-DMAP / CH₂Cl₂ / 2 h / 23 °C

6.1: MeLi; HMPA / tetrahydrofuran; diethyl ether / 5 h / -50 °C

6.2: CuCN / tetrahydrofuran; diethyl ether / 0.75 h / 0 °C

6.3: 70 percent / tetrahydrofuran; diethyl ether / 16 h / -50 - 23 °C

7.1: 80 percent / (R)-N-p-toluenesulfonyl-β-methyltryptophan; BH3*THF / CH2Cl2 / 48 h / -78 °C

8.1: NaBH₄ / tetrahydrofuran; H₂O / 0.08 h / 23 °C

9.1: NaOMe / propan-2-ol / 30 h / -30 - 0 °C

10.1: aq. LiOH / ethanol; propan-2-ol / 72 h / 70 °C

11.1: CF₃CO₂H / CH₂Cl₂ / 3.5 h / 23 °C

11.2: KF; KHCO₃; aq. H₂O₂ / tetrahydrofuran; methanol / 24 h / 23 °C

12.1: 87 percent / CSA / tetrahydrofuran / 14 h / 23 °C

13.1: 88 percent / Al(OtBu)3; t-BuOOH / toluene / 2 h / 23 °C

14.1: o-nitrophenylselenocyante; Bu₃P / benzene / 2 h / 75 °C

14.2: 82 percent / aq. H₂O₂ / benzene; tetrahydrofuran / 7 h / 0 °C

15.1: 86 percent / Pd(OAc)2 / 24 h / 23 °C / 760.05 Torr

16.1: 98 percent / NaIO₄; CSA / methanol; H₂O / 7 h / 23 °C

With pyridine; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; palladium diacetate; lithium hydroxide; sodium tetrahydroborate; sodium periodate; Schwartz's reagent; n-butyllithium; ortho-nitrophenyl selenocyanate; borane-THF; tributylphosphine; (2S,3R)-3-(1H-indol-3-yl)-2-((4-methylphenyl)sulfonamido)butanoic acid; camphor-10-sulfonic acid; methyllithium; sodium methylate; diisobutylaluminium hydride; aluminum tri-tert-butoxide; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; isopropyl alcohol; toluene; benzene;

DOI:10.1021/ja004043r

Reference yield:

2E,6E,10E-geranylgeranyl methanesulfonate (71668-80-9) → eunicenone A (152340-70-0)

Guidance literature:

Multi-step reaction with 15 steps

1.1: CuCN / tetrahydrofuran / 1 h / -40 - 0 °C

1.2: 427 mg / tetrahydrofuran; hexane / 12 h / 0 °C

2.1: Cp₂ZrHCl / tetrahydrofuran / 0.75 h / 20 °C

2.2: 75 percent / ZnCl₂ / Pd(PPh₃)4 / tetrahydrofuran / 1 h / 20 °C

3.1: DIBAL-H / tetrahydrofuran; toluene / 0.67 h / -78 - 0 °C

3.2: MeOH; Na₂SO₄*10H₂O / tetrahydrofuran / 0.5 h / 23 °C

4.1: pyridine; 4-DMAP / CH₂Cl₂ / 2 h / 23 °C

5.1: MeLi; HMPA / tetrahydrofuran; diethyl ether / 5 h / -50 °C

5.2: CuCN / tetrahydrofuran; diethyl ether / 0.75 h / 0 °C

5.3: 70 percent / tetrahydrofuran; diethyl ether / 16 h / -50 - 23 °C

6.1: 80 percent / (R)-N-p-toluenesulfonyl-β-methyltryptophan; BH3*THF / CH2Cl2 / 48 h / -78 °C

7.1: NaBH₄ / tetrahydrofuran; H₂O / 0.08 h / 23 °C

8.1: NaOMe / propan-2-ol / 30 h / -30 - 0 °C

9.1: aq. LiOH / ethanol; propan-2-ol / 72 h / 70 °C

10.1: CF₃CO₂H / CH₂Cl₂ / 3.5 h / 23 °C

10.2: KF; KHCO₃; aq. H₂O₂ / tetrahydrofuran; methanol / 24 h / 23 °C

11.1: 87 percent / CSA / tetrahydrofuran / 14 h / 23 °C

12.1: 88 percent / Al(OtBu)3; t-BuOOH / toluene / 2 h / 23 °C

13.1: o-nitrophenylselenocyante; Bu₃P / benzene / 2 h / 75 °C

13.2: 82 percent / aq. H₂O₂ / benzene; tetrahydrofuran / 7 h / 0 °C

14.1: 86 percent / Pd(OAc)2 / 24 h / 23 °C / 760.05 Torr

15.1: 98 percent / NaIO₄; CSA / methanol; H₂O / 7 h / 23 °C

With pyridine; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; palladium diacetate; lithium hydroxide; sodium tetrahydroborate; sodium periodate; Schwartz's reagent; ortho-nitrophenyl selenocyanate; borane-THF; tributylphosphine; (2S,3R)-3-(1H-indol-3-yl)-2-((4-methylphenyl)sulfonamido)butanoic acid; camphor-10-sulfonic acid; methyllithium; sodium methylate; diisobutylaluminium hydride; aluminum tri-tert-butoxide; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; isopropyl alcohol; toluene; benzene;

DOI:10.1021/ja004043r

upstream raw materials:

[(7S,10R,11R)-10-Hydroxy-11-((2E,6E,10E)-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraenyl)-6,14-dioxa-dispiro[4.1.5.2]tetradec-8-en-8-yl]-acetic acid methyl ester

Geranylgeraniol

2E,6E,10E-geranylgeranyl methanesulfonate

geranylgeranylacetylene

Refernces