(3aR,3bS,4S,6aR,7R)-3,3a,5,5-Tetramethyl-3-phenylselanyl-4,7-bis-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one

Base Information

• Chemical Name: (3aR,3bS,4S,6aR,7R)-3,3a,5,5-Tetramethyl-3-phenylselanyl-4,7-bis-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one
• CAS No.: 85031-56-7
• Molecular Formula: C₃₁H₄₂O₅Se
• Molecular Weight: 573.631
• Mol file: 85031-56-7.mol

Synonyms:

Chemical Property of (3aR,3bS,4S,6aR,7R)-3,3a,5,5-Tetramethyl-3-phenylselanyl-4,7-bis-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,3bS,4S,6aR,7R)-3,3a,5,5-Tetramethyl-3-phenylselanyl-4,7-bis-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one

There total 17 articles about (3aR,3bS,4S,6aR,7R)-3,3a,5,5-Tetramethyl-3-phenylselanyl-4,7-bis-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one 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:

(2aSR,4RS,4aSR,6aSR,6bRS)-octahydro-6,6-dimethyl-2-oxo-2H-pentaleno<1,6-bc>furan-4-carboxylic acid (82873-74-3) → (3aR,3bS,4S,6aR,7R)-3,3a,5,5-Tetramethyl-3-phenylselanyl-4,7-bis-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one (85031-56-7)

Guidance literature:

Multi-step reaction with 19 steps

1: 1.) pyridine, Cu(OAc)2; 2.) Pb(OAc)4 / 1.) benzene, 30 min; 2a.) 2.5 h, dark, b.) benzene, reflux, 30 min

2: 1.) t-AmONa; 2.) water / 1.) DMSO, 18 h, r.t.; 2.) 6 h; 3.) 24 h

3: 92 percent / Jones reagent / acetone / 0.5 h / 0 °C

4: 23.9 percent / 0.82 M AlH₃ / tetrahydrofuran / 3 h / 0 °C

5: 86 percent / LiCl, methanesulfonyl chloride / dimethylformamide; various solvent(s) / 1.5 h / 0 °C

6: 8.0 g / LiAlH₄ / tetrahydrofuran / 5 h / Ambient temperature

7: 95 percent / pyridine / 12 h / 0 °C

8: 82 percent / KO₂ / dibenzo-18-crown-6-ether / 1,2-dimethoxy-ethane; dimethylsulfoxide / 48 h / Ambient temperature

9: 96 percent / pyridine / 6 h / Ambient temperature

10: 1.) BH₃; 2.) 2 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C, 3 h; 2.) water, 10 min

11: 78 percent / Jones reagent / acetone / 0.5 h / 0 °C

12: 80 percent / 1 M t-BuOK / benzene; 2-methyl-propan-2-ol / Heating

13: 99 percent / Hg(II) salt / 0.17 h / Ambient temperature

14: 60 percent / 5percent KOH / methanol / 24 h / Heating

15: p-TsOH / 24 h / Heating

16: 1.) mCPBA, NaHCO₃; 2.) water, Na₂CO₃; 3.) 1 N LiOH / 1.) THF, 15 min; 2.) reflux, 20 h; 3.) 40 deg C, 3 h

17: 190 mg / p-TsOH / CHCl₃; tetrahydrofuran / 0.25 h

18: 1.) LDA / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C, 30 min

19: 1.) LDA / 1.) THF, -78 deg C, 50 min; 2.) THF, -78 deg C, 30 min

With pyridine; aluminium hydride; lead(IV) acetate; potassium hydroxide; lithium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; jones reagent; copper diacetate; Hg(II) salt; borane; potassium tert-butylate; water; dihydrogen peroxide; sodium tert-pentoxide; sodium hydrogencarbonate; sodium carbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; lithium chloride; lithium diisopropyl amide; dibenzo-18-crown-6; In tetrahydrofuran; pyridine; methanol; 1,2-dimethoxyethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;

DOI:10.1016/0040-4020(84)85126-1

Reference yield:

cis-3,3a,4,5,6,6a-hexahydro-5,5-dimethyl-6-oxo-1-pentalenecarboxylic acid methyl ester (90546-09-1) → (3aR,3bS,4S,6aR,7R)-3,3a,5,5-Tetramethyl-3-phenylselanyl-4,7-bis-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one (85031-56-7)

Guidance literature:

Multi-step reaction with 16 steps

1: 23.9 percent / 0.82 M AlH₃ / tetrahydrofuran / 3 h / 0 °C

2: 86 percent / LiCl, methanesulfonyl chloride / dimethylformamide; various solvent(s) / 1.5 h / 0 °C

3: 8.0 g / LiAlH₄ / tetrahydrofuran / 5 h / Ambient temperature

4: 95 percent / pyridine / 12 h / 0 °C

5: 82 percent / KO₂ / dibenzo-18-crown-6-ether / 1,2-dimethoxy-ethane; dimethylsulfoxide / 48 h / Ambient temperature

6: 96 percent / pyridine / 6 h / Ambient temperature

7: 1.) BH₃; 2.) 2 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C, 3 h; 2.) water, 10 min

8: 78 percent / Jones reagent / acetone / 0.5 h / 0 °C

9: 80 percent / 1 M t-BuOK / benzene; 2-methyl-propan-2-ol / Heating

10: 99 percent / Hg(II) salt / 0.17 h / Ambient temperature

11: 60 percent / 5percent KOH / methanol / 24 h / Heating

12: p-TsOH / 24 h / Heating

13: 1.) mCPBA, NaHCO₃; 2.) water, Na₂CO₃; 3.) 1 N LiOH / 1.) THF, 15 min; 2.) reflux, 20 h; 3.) 40 deg C, 3 h

14: 190 mg / p-TsOH / CHCl₃; tetrahydrofuran / 0.25 h

15: 1.) LDA / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C, 30 min

16: 1.) LDA / 1.) THF, -78 deg C, 50 min; 2.) THF, -78 deg C, 30 min

With aluminium hydride; potassium hydroxide; lithium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; jones reagent; Hg(II) salt; borane; potassium tert-butylate; water; dihydrogen peroxide; sodium hydrogencarbonate; sodium carbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; lithium chloride; lithium diisopropyl amide; dibenzo-18-crown-6; In tetrahydrofuran; pyridine; methanol; 1,2-dimethoxyethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;

DOI:10.1016/0040-4020(84)85126-1

Reference yield:

(3aRS,6SR,6aRS)-3,3a,4,5,6,6a-hexahydro-6-methanesulfonyloxy-1,5,5-trimethylpentalene (82873-78-7) → (3aR,3bS,4S,6aR,7R)-3,3a,5,5-Tetramethyl-3-phenylselanyl-4,7-bis-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one (85031-56-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 82 percent / KO₂ / dibenzo-18-crown-6-ether / 1,2-dimethoxy-ethane; dimethylsulfoxide / 48 h / Ambient temperature

2: 96 percent / pyridine / 6 h / Ambient temperature

3: 1.) BH₃; 2.) 2 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C, 3 h; 2.) water, 10 min

4: 78 percent / Jones reagent / acetone / 0.5 h / 0 °C

5: 80 percent / 1 M t-BuOK / benzene; 2-methyl-propan-2-ol / Heating

6: 99 percent / Hg(II) salt / 0.17 h / Ambient temperature

7: 60 percent / 5percent KOH / methanol / 24 h / Heating

8: p-TsOH / 24 h / Heating

9: 1.) mCPBA, NaHCO₃; 2.) water, Na₂CO₃; 3.) 1 N LiOH / 1.) THF, 15 min; 2.) reflux, 20 h; 3.) 40 deg C, 3 h

10: 190 mg / p-TsOH / CHCl₃; tetrahydrofuran / 0.25 h

11: 1.) LDA / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C, 30 min

12: 1.) LDA / 1.) THF, -78 deg C, 50 min; 2.) THF, -78 deg C, 30 min

With potassium hydroxide; lithium hydroxide; sodium hydroxide; jones reagent; Hg(II) salt; borane; potassium tert-butylate; water; dihydrogen peroxide; sodium hydrogencarbonate; sodium carbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; dibenzo-18-crown-6; In tetrahydrofuran; pyridine; methanol; 1,2-dimethoxyethane; chloroform; dimethyl sulfoxide; acetone; tert-butyl alcohol; benzene;

DOI:10.1016/0040-4020(84)85126-1

upstream raw materials:

Phenylselenyl bromide

(3aRS,3bRS,4RS,6aSR,7SR)-3,3a,3b,4,5,6,6a,7-octahydro-3,3a,5,5-tetramethyl-4,7-bis<(tetrahydro-2H-pyran-2-yl)oxy>-2H-cyclopentapentalen-2-one

(3α,3aα,3bβ,7aα)-2,3,3a,3b,4,5,7,7a-octahydro-3-hydroxy-2,2,3b-trimethyl-5-oxo-1H-cyclopentapentalene

(2aSR,4RS,4aSR,6aSR,6bRS)-octahydro-6,6-dimethyl-2-oxo-2H-pentaleno<1,6-bc>furan-4-carboxylic acid