2,2-Dimethyl-propionic acid (1S,2S,3S)-3-isopropenyl-2-methyl-2-(2-phenylselanylcarbonyl-ethyl)-cyclopentyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (1S,2S,3S)-3-isopropenyl-2-methyl-2-(2-phenylselanylcarbonyl-ethyl)-cyclopentyl ester
• CAS No.: 212915-61-2
• Molecular Formula: C₂₃H₃₂O₃Se
• Molecular Weight: 435.465
• Mol file: 212915-61-2.mol

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid (1S,2S,3S)-3-isopropenyl-2-methyl-2-(2-phenylselanylcarbonyl-ethyl)-cyclopentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (1S,2S,3S)-3-isopropenyl-2-methyl-2-(2-phenylselanylcarbonyl-ethyl)-cyclopentyl ester

There total 11 articles about 2,2-Dimethyl-propionic acid (1S,2S,3S)-3-isopropenyl-2-methyl-2-(2-phenylselanylcarbonyl-ethyl)-cyclopentyl ester 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:

(7aS)-(+)-4,7a-dimethyl-2,3,7,7a-tetrahydro-1H-indene-1,5(6H)-dione (33878-96-5) → 2,2-Dimethyl-propionic acid (1S,2S,3S)-3-isopropenyl-2-methyl-2-(2-phenylselanylcarbonyl-ethyl)-cyclopentyl ester (212915-61-2)

Guidance literature:

Multi-step reaction with 13 steps

1: 98 percent / Li(t-BuO)3AlH / tetrahydrofuran

2: 90 percent / 4-DMAP / pyridine / 0 deg C to r.t.

3: 80 percent / NaBH₄, CeCl₃ / methanol / 0 deg C to r.t.

4: Et₃N, 4-DMAP / CH₂Cl₂ / Ambient temperature

5: Na(CN)BH₃, Bu₃SnCl, AIBN / 2-methyl-propan-2-ol / Heating

6: KHCO₃, 30percent H₂O₂ / tetrahydrofuran; methanol / Heating

7: 99 percent / 7percent aq. NaOCl / acetic acid / Ambient temperature

8: 1.) m-CPBA, KHCO₃; 2.) LiOH / 1.) CH₂Cl₂, r.t.; 2.) aq. THF, reflux

9: diethyl ether / Ambient temperature

10: 99 percent / toluene / Heating

11: 70 percent / (EtO)3P / Heating

12: LiOH / H₂O; tetrahydrofuran / Heating

13: Bu₃P / tetrahydrofuran / Ambient temperature

With dmap; lithium hydroxide; sodium hypochlorite; sodium tetrahydroborate; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); tributylphosphine; tributyltin chloride; dihydrogen peroxide; sodium cyanoborohydride; potassium hydrogencarbonate; lithium tri-t-butoxyaluminum hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triethyl phosphite; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; acetic acid; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4039(98)01180-0

Reference yield:

(1S,7aS)-(+)-1-hydroxy-4,7a-dimethyl-2,3,7,7a-tetrahydro-1H-indene-5(6)-one (212953-00-9) → 2,2-Dimethyl-propionic acid (1S,2S,3S)-3-isopropenyl-2-methyl-2-(2-phenylselanylcarbonyl-ethyl)-cyclopentyl ester (212915-61-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 90 percent / 4-DMAP / pyridine / 0 deg C to r.t.

2: 80 percent / NaBH₄, CeCl₃ / methanol / 0 deg C to r.t.

3: Et₃N, 4-DMAP / CH₂Cl₂ / Ambient temperature

4: Na(CN)BH₃, Bu₃SnCl, AIBN / 2-methyl-propan-2-ol / Heating

5: KHCO₃, 30percent H₂O₂ / tetrahydrofuran; methanol / Heating

6: 99 percent / 7percent aq. NaOCl / acetic acid / Ambient temperature

7: 1.) m-CPBA, KHCO₃; 2.) LiOH / 1.) CH₂Cl₂, r.t.; 2.) aq. THF, reflux

8: diethyl ether / Ambient temperature

9: 99 percent / toluene / Heating

10: 70 percent / (EtO)3P / Heating

11: LiOH / H₂O; tetrahydrofuran / Heating

12: Bu₃P / tetrahydrofuran / Ambient temperature

With dmap; lithium hydroxide; sodium hypochlorite; sodium tetrahydroborate; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); tributylphosphine; tributyltin chloride; dihydrogen peroxide; sodium cyanoborohydride; potassium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triethyl phosphite; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; acetic acid; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4039(98)01180-0

Reference yield:

2,2-Dimethyl-propionic acid (1S,5S,7aS)-5-hydroxy-4,7a-dimethyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-yl ester (212915-50-9) → 2,2-Dimethyl-propionic acid (1S,2S,3S)-3-isopropenyl-2-methyl-2-(2-phenylselanylcarbonyl-ethyl)-cyclopentyl ester (212915-61-2)

Guidance literature:

Multi-step reaction with 10 steps

1: Et₃N, 4-DMAP / CH₂Cl₂ / Ambient temperature

2: Na(CN)BH₃, Bu₃SnCl, AIBN / 2-methyl-propan-2-ol / Heating

3: KHCO₃, 30percent H₂O₂ / tetrahydrofuran; methanol / Heating

4: 99 percent / 7percent aq. NaOCl / acetic acid / Ambient temperature

5: 1.) m-CPBA, KHCO₃; 2.) LiOH / 1.) CH₂Cl₂, r.t.; 2.) aq. THF, reflux

6: diethyl ether / Ambient temperature

7: 99 percent / toluene / Heating

8: 70 percent / (EtO)3P / Heating

9: LiOH / H₂O; tetrahydrofuran / Heating

10: Bu₃P / tetrahydrofuran / Ambient temperature

With dmap; lithium hydroxide; sodium hypochlorite; 2,2'-azobis(isobutyronitrile); tributylphosphine; tributyltin chloride; dihydrogen peroxide; sodium cyanoborohydride; potassium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triethyl phosphite; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4039(98)01180-0

upstream raw materials:

N-phenylselanylphthalimide

2,2-Dimethyl-propionic acid (1S,2S,3S)-2-(2-carboxy-ethyl)-3-isopropenyl-2-methyl-cyclopentyl ester

(1S,7aS)-(+)-1-hydroxy-4,7a-dimethyl-2,3,7,7a-tetrahydro-1H-indene-5⁽⁶⁾-one

(7aS)-(+)-4,7a-dimethyl-2,3,7,7a-tetrahydro-1H-indene-1,5(6H)-dione