(3aR,3bS,4S,6aR,7R)-7-Hydroxy-3,3a,5,5-tetramethyl-3-phenylselanyl-4-(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)-7-Hydroxy-3,3a,5,5-tetramethyl-3-phenylselanyl-4-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one
• CAS No.: 82873-85-6
• Molecular Formula: C₂₆H₃₄O₄Se
• Molecular Weight: 489.514
• Mol file: 82873-85-6.mol

Synonyms:

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

There total 20 articles about (3aR,3bS,4S,6aR,7R)-7-Hydroxy-3,3a,5,5-tetramethyl-3-phenylselanyl-4-(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:

(2aS,4R,4aS,6aS,6bR)-2-Hydroxy-6,6-dimethyl-octahydro-pentaleno[1,6-bc]furan-4-carbaldehyde (82873-73-2) → (3aR,3bS,4S,6aR,7R)-7-Hydroxy-3,3a,5,5-tetramethyl-3-phenylselanyl-4-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one (82873-85-6)

Guidance literature:

Multi-step reaction with 19 steps

1: Jones reagent / Ambient temperature

4: 85 percent / Jones reagent

5: 85 percent / LiAl(O-t-Bu)3H

6: LiCl, γ-collidine / dimethylformamide / 1 h / 0 °C

7: LiAlH₄ / tetrahydrofuran / 16 h / Ambient temperature

8: pyridine

9: 1.) KO₂, dibenzo-18-crown-6-ether, 2.) NaBH₄, water / 1.) DMSO, DME, room temp., 48 h

11: 1.) BH₃*THF, H₂O₂, OH^(1-) 2.) Jones reagent

12: t-BuOK / benzene; 2-methyl-propan-2-ol / Heating

13: mercuric acetate / formic acid / 0.25 h / Ambient temperature

14: 1.) 5percent methanolic KOH 2.) Al₂O₃

15: 90 percent / p-TsOH / 24 h / Heating

16: 1.) mCPBA, 2.) NaHCO₃, 1N-LiOH / 1.) THF, 0 deg C, 15 min 2.) water

18: LDA / 1.) -78 deg C, 30 min 2.) warming up to 0 deg C

19: LDA / 1.) -78 deg C, 30 min 2.) warming up to 0 deg C

With pyridine; 2,4,6-trimethyl-pyridine; aluminum oxide; potassium hydroxide; lithium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; dibenzo-18-crown-6; jones reagent; borane-THF; potassium tert-butylate; mercury(II) diacetate; water; hydroxide; dihydrogen peroxide; sodium hydrogencarbonate; toluene-4-sulfonic acid; lithium tri-t-butoxyaluminum hydride; 3-chloro-benzenecarboperoxoic acid; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; formic acid; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4039(00)87199-3

Reference yield:

(3aRS,6SR,6aRS)-3,3a,4,5,6,6a-hexahydro-6-hydroxy-5,5-dimethyl-1-pentalenecarboxylic acid methyl ester (82873-76-5,90546-14-8) → (3aR,3bS,4S,6aR,7R)-7-Hydroxy-3,3a,5,5-tetramethyl-3-phenylselanyl-4-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one (82873-85-6)

Guidance literature:

Multi-step reaction with 16 steps

1: 85 percent / Jones reagent

2: 85 percent / LiAl(O-t-Bu)3H

3: LiCl, γ-collidine / dimethylformamide / 1 h / 0 °C

4: LiAlH₄ / tetrahydrofuran / 16 h / Ambient temperature

5: pyridine

6: 1.) KO₂, dibenzo-18-crown-6-ether, 2.) NaBH₄, water / 1.) DMSO, DME, room temp., 48 h

8: 1.) BH₃*THF, H₂O₂, OH^(1-) 2.) Jones reagent

9: t-BuOK / benzene; 2-methyl-propan-2-ol / Heating

10: mercuric acetate / formic acid / 0.25 h / Ambient temperature

11: 1.) 5percent methanolic KOH 2.) Al₂O₃

12: 90 percent / p-TsOH / 24 h / Heating

13: 1.) mCPBA, 2.) NaHCO₃, 1N-LiOH / 1.) THF, 0 deg C, 15 min 2.) water

15: LDA / 1.) -78 deg C, 30 min 2.) warming up to 0 deg C

16: LDA / 1.) -78 deg C, 30 min 2.) warming up to 0 deg C

With pyridine; 2,4,6-trimethyl-pyridine; aluminum oxide; potassium hydroxide; lithium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; dibenzo-18-crown-6; jones reagent; borane-THF; potassium tert-butylate; mercury(II) diacetate; water; hydroxide; dihydrogen peroxide; sodium hydrogencarbonate; toluene-4-sulfonic acid; lithium tri-t-butoxyaluminum hydride; 3-chloro-benzenecarboperoxoic acid; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; formic acid; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4039(00)87199-3

Reference yield:

(2aRS,4aSR,6aSR,6bRS)-2a,4a,5,6,6a,6b-hexahydro-6,6-dimethyl-2H-pentaleno<1,6-bc>furan-2-one (82873-75-4) → (3aR,3bS,4S,6aR,7R)-7-Hydroxy-3,3a,5,5-tetramethyl-3-phenylselanyl-4-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one (82873-85-6)

Guidance literature:

Multi-step reaction with 17 steps

2: 85 percent / Jones reagent

3: 85 percent / LiAl(O-t-Bu)3H

4: LiCl, γ-collidine / dimethylformamide / 1 h / 0 °C

5: LiAlH₄ / tetrahydrofuran / 16 h / Ambient temperature

6: pyridine

7: 1.) KO₂, dibenzo-18-crown-6-ether, 2.) NaBH₄, water / 1.) DMSO, DME, room temp., 48 h

9: 1.) BH₃*THF, H₂O₂, OH^(1-) 2.) Jones reagent

10: t-BuOK / benzene; 2-methyl-propan-2-ol / Heating

11: mercuric acetate / formic acid / 0.25 h / Ambient temperature

12: 1.) 5percent methanolic KOH 2.) Al₂O₃

13: 90 percent / p-TsOH / 24 h / Heating

14: 1.) mCPBA, 2.) NaHCO₃, 1N-LiOH / 1.) THF, 0 deg C, 15 min 2.) water

16: LDA / 1.) -78 deg C, 30 min 2.) warming up to 0 deg C

17: LDA / 1.) -78 deg C, 30 min 2.) warming up to 0 deg C

With pyridine; 2,4,6-trimethyl-pyridine; aluminum oxide; potassium hydroxide; lithium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; dibenzo-18-crown-6; jones reagent; borane-THF; potassium tert-butylate; mercury(II) diacetate; water; hydroxide; dihydrogen peroxide; sodium hydrogencarbonate; toluene-4-sulfonic acid; lithium tri-t-butoxyaluminum hydride; 3-chloro-benzenecarboperoxoic acid; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; formic acid; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4039(00)87199-3

upstream raw materials:

Phenylselenyl bromide

(3aR,3bR,4R,6aS,7S)-7-Hydroxy-3,3a,5,5-tetramethyl-4-(tetrahydro-pyran-2-yloxy)-3,3a,3b,4,5,6,6a,7-octahydro-cyclopenta[a]pentalen-2-one

3,4-dihydro-2H-pyran

(2aRS,4aSR,6aSR,6bRS)-2a,4a,5,6,6a,6b-hexahydro-6,6-dimethyl-2H-pentaleno<1,6-bc>furan-2-one