(3R,5R)-5-Benzyloxymethyl-3-methyl-2-phenylselanyl-cyclohexanone

Base Information

• Chemical Name: (3R,5R)-5-Benzyloxymethyl-3-methyl-2-phenylselanyl-cyclohexanone
• CAS No.: 130256-42-7
• Molecular Formula: C₂₁H₂₄O₂Se
• Molecular Weight: 387.38
• Mol file: 130256-42-7.mol

Synonyms:(3R,5R)-5-Benzyloxymethyl-3-methyl-2-phenylselanyl-cyclohexanone

Chemical Property of (3R,5R)-5-Benzyloxymethyl-3-methyl-2-phenylselanyl-cyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R)-5-Benzyloxymethyl-3-methyl-2-phenylselanyl-cyclohexanone

There total 12 articles about (3R,5R)-5-Benzyloxymethyl-3-methyl-2-phenylselanyl-cyclohexanone 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:

2,5,11-trioxatricyclo[4.3.1.14,8 ] undecan-3-one (50409-13-7) → (3R,5R)-5-Benzyloxymethyl-3-methyl-2-phenylselanyl-cyclohexanone (130256-42-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 90 percent / NaBH₄ / ethanol / Ambient temperature

2: 73 percent / t.BuOK / 2-methyl-propan-2-ol / 65 °C

3: 96 percent / (COCl)2, DMSO / CH₂Cl₂ / -60 °C

4: 64 percent / Zn, TiCl₄ / tetrahydrofuran; CH₂Cl₂ / 0 °C

5: 88 percent / BH_3.THF, NaOH, H₂O₂ / tetrahydrofuran / Ambient temperature

6: 86 percent / t.BuOK / tetrahydrofuran / 65 °C

7: 96 percent / 10 percent aq. HCl / tetrahydrofuran / 18 h / Ambient temperature

8: Py, DMAP / Ambient temperature

9: 73 percent / pig liver esterase, NaOH / 35 °C / phosphate buffer at pH 7

10: 1) (COCl)2, DMSO, 2) DBU / 1) CH₂Cl₃, -60 deg C, 2) CH₂Cl₂, rt

11: 1) ether, 0 deg C, 2) ether

With pyridine; hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; pig liver esterase; borane-THF; oxalyl dichloride; potassium tert-butylate; dihydrogen peroxide; titanium tetrachloride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc; In tetrahydrofuran; ethanol; dichloromethane; tert-butyl alcohol;

DOI:10.1016/S0957-4166(00)82266-1

Reference yield:

cis,cis-1,3,5-trihydroxycyclohexane (50409-12-6,13314-30-2) → (3R,5R)-5-Benzyloxymethyl-3-methyl-2-phenylselanyl-cyclohexanone (130256-42-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 84 percent / Amberlyst-15 / 1,2-dimethoxy-ethane / 2 h / 85 °C

2: 90 percent / NaBH₄ / ethanol / Ambient temperature

3: 73 percent / t.BuOK / 2-methyl-propan-2-ol / 65 °C

4: 96 percent / (COCl)2, DMSO / CH₂Cl₂ / -60 °C

5: 64 percent / Zn, TiCl₄ / tetrahydrofuran; CH₂Cl₂ / 0 °C

6: 88 percent / BH_3.THF, NaOH, H₂O₂ / tetrahydrofuran / Ambient temperature

7: 86 percent / t.BuOK / tetrahydrofuran / 65 °C

8: 96 percent / 10 percent aq. HCl / tetrahydrofuran / 18 h / Ambient temperature

9: Py, DMAP / Ambient temperature

10: 73 percent / pig liver esterase, NaOH / 35 °C / phosphate buffer at pH 7

11: 1) (COCl)2, DMSO, 2) DBU / 1) CH₂Cl₃, -60 deg C, 2) CH₂Cl₂, rt

12: 1) ether, 0 deg C, 2) ether

With pyridine; hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; pig liver esterase; amberlyst-15; borane-THF; oxalyl dichloride; potassium tert-butylate; dihydrogen peroxide; titanium tetrachloride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; tert-butyl alcohol;

DOI:10.1016/S0957-4166(00)82266-1

Reference yield:

(1S,5R,7R)-3-Hydroxymethyl-2,4-dioxa-bicyclo[3.3.1]nonan-7-ol (130323-27-2) → (3R,5R)-5-Benzyloxymethyl-3-methyl-2-phenylselanyl-cyclohexanone (130256-42-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 73 percent / t.BuOK / 2-methyl-propan-2-ol / 65 °C

2: 96 percent / (COCl)2, DMSO / CH₂Cl₂ / -60 °C

3: 64 percent / Zn, TiCl₄ / tetrahydrofuran; CH₂Cl₂ / 0 °C

4: 88 percent / BH_3.THF, NaOH, H₂O₂ / tetrahydrofuran / Ambient temperature

5: 86 percent / t.BuOK / tetrahydrofuran / 65 °C

6: 96 percent / 10 percent aq. HCl / tetrahydrofuran / 18 h / Ambient temperature

7: Py, DMAP / Ambient temperature

8: 73 percent / pig liver esterase, NaOH / 35 °C / phosphate buffer at pH 7

9: 1) (COCl)2, DMSO, 2) DBU / 1) CH₂Cl₃, -60 deg C, 2) CH₂Cl₂, rt

10: 1) ether, 0 deg C, 2) ether

With pyridine; hydrogenchloride; dmap; sodium hydroxide; pig liver esterase; borane-THF; oxalyl dichloride; potassium tert-butylate; dihydrogen peroxide; titanium tetrachloride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;

DOI:10.1016/S0957-4166(00)82266-1

upstream raw materials:

Phenylselenyl chloride

lithium dimethylcuprate

(R)-5-benzyloxymethyl-2-cyclohexenone

2,5,11-trioxatricyclo[4.3.1.14,8 ] undecan-3-one

Downstream raw materials:

(R)-5-(benzyloxymethyl)-3-methylcyclohex-2-enone

Refernces