(23R)-23-[(1S,2S)-2-Methylcyclopropyl]-26,27-dinorcholest-5-en-3β-ol

Base Information

• Chemical Name: (23R)-23-[(1S,2S)-2-Methylcyclopropyl]-26,27-dinorcholest-5-en-3β-ol
• CAS No.: 114174-00-4
• Molecular Formula: C₂₉H₄₈O
• Molecular Weight: 412.7
• Mol file: 114174-00-4.mol

Synonyms:26,27-Dinorcholest-5-en-3-ol,23-(2-methylcyclopropyl)-, [3b,23R(1S,2S)]-; Hebesterol

Chemical Property of (23R)-23-[(1S,2S)-2-Methylcyclopropyl]-26,27-dinorcholest-5-en-3β-ol

Chemical Property:

• PSA: 20.23000
• LogP: 7.63470

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (23R)-23-[(1S,2S)-2-Methylcyclopropyl]-26,27-dinorcholest-5-en-3β-ol

There total 56 articles about (23R)-23-[(1S,2S)-2-Methylcyclopropyl]-26,27-dinorcholest-5-en-3β-ol 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:

(20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde (25819-77-6) → (23S,24R,25R)-23-ethyl-24,26-cyclocholest-5-en-3β-ol (114174-00-4,114247-93-7,114247-94-8,114247-95-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 87 percent / toluene / 15 h / Heating

2: 100 percent / H₂ / Pd-C (10percent) / ethyl acetate / 2 h

3: 1.) LDA; / 1.) THF-10percent HMPA, -70 deg C, 30 min; 2.) -70 deg C, 10 min

4: 88 percent / LiAlH₄ / diethyl ether / 0.5 h / Ambient temperature

5: 92 percent / PCC / CH₂Cl₂ / 1 h

6: 94 percent / tetrahydrofuran / 1 h / 0 °C

7: 95 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 7 h / Ambient temperature

8: 1.) lithium diphenylphosphide; 2.) MeI / 1.) THF, room temp., 10 h; 2.) room temp., 30 min

9: benzyltriethylammonium chloride (BTEAC), NaOH (50percent) / H₂O / 36 h / Ambient temperature

10: Li / liquid ammonia; diethyl ether / 5 h / -70 °C

11: toluene-p-sulphonic acid / dioxane; H₂O / 1 h / Heating

With sodium hydroxide; lithium aluminium tetrahydride; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; lithium; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium diphenylphosphide; lithium diisopropyl amide; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; ammonia; water; ethyl acetate; toluene;

Reference yield:

(20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde (25819-77-6) → (23S,24S,25S)-23-ethyl-24,26-cyclocholest-5-en-3β-ol (114174-00-4,114247-93-7,114247-94-8,114247-95-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 87 percent / toluene / 15 h / Heating

2: 100 percent / H₂ / Pd-C (10percent) / ethyl acetate / 2 h

3: 1.) LDA; / 1.) THF-10percent HMPA, -70 deg C, 30 min; 2.) -70 deg C, 10 min

4: 88 percent / LiAlH₄ / diethyl ether / 0.5 h / Ambient temperature

5: 92 percent / PCC / CH₂Cl₂ / 1 h

6: 94 percent / tetrahydrofuran / 1 h / 0 °C

7: 95 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 7 h / Ambient temperature

8: 1.) lithium diphenylphosphide; 2.) MeI / 1.) THF, room temp., 10 h; 2.) room temp., 30 min

9: benzyltriethylammonium chloride (BTEAC), NaOH (50percent) / H₂O / 36 h / Ambient temperature

10: Li / liquid ammonia; diethyl ether / 5 h / -70 °C

11: toluene-p-sulphonic acid / dioxane; H₂O / 1 h / Heating

With sodium hydroxide; lithium aluminium tetrahydride; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; lithium; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium diphenylphosphide; lithium diisopropyl amide; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; ammonia; water; ethyl acetate; toluene;

Reference yield:

(20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde (25819-77-6) → (23R,24R,25R)-23-ethyl-24,26-cyclocholest-5-en-3β-ol (114174-00-4,114247-93-7,114247-94-8,114247-95-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 87 percent / toluene / 15 h / Heating

2: 100 percent / H₂ / Pd-C (10percent) / ethyl acetate / 2 h

3: 1.) LDA; / 1.) THF-10percent HMPA, -70 deg C, 30 min; 2.) -70 deg C, 10 min

4: 88 percent / LiAlH₄ / diethyl ether / 0.5 h / Ambient temperature

5: 92 percent / PCC / CH₂Cl₂ / 1 h

6: 94 percent / tetrahydrofuran / 1 h / 0 °C

7: 95 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 7 h / Ambient temperature

8: 1.) lithium diphenylphosphide; 2.) MeI / 1.) THF, room temp., 10 h; 2.) room temp., 30 min

9: 83 percent / benzyltriethylammonium chloride (BTEAC), NaOH (50percent) / H₂O / 36 h / Ambient temperature

10: Li / liquid ammonia; diethyl ether / 5 h / -70 °C

11: toluene-p-sulphonic acid / dioxane; H₂O / 1 h / Heating

With sodium hydroxide; lithium aluminium tetrahydride; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; lithium; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium diphenylphosphide; lithium diisopropyl amide; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; ammonia; water; ethyl acetate; toluene;

upstream raw materials:

(23S,24R,25R)-23-ethyl-6β-methoxy-3α,5:24,26-dicyclocholestane

(20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde

(23S,24S,25S)-24,25-(dichloromethylene)-23-ethyl-6β-methoxy-3α,5-cyclocholestane

23ξ-ethyl-6β-methoxy-3α,5-cyclocholan-24-ol

Downstream raw materials:

Stigmasterol

(E)-23-ethylcholesta-5,22-dien-3β-ol

(23S)-23-ethylcholesta-5,24-dien-3β-ol

(23S,24R)-23-ethyl-24-methyl-27-norcholesta-5,25-dien-3β-ol

Refernces