29-Fluorostigmasterol

Base Information

• Chemical Name: 29-Fluorostigmasterol
• CAS No.: 87028-22-6
• Molecular Formula: C₂₉H₄₇FO
• Molecular Weight: 430.69
• Mol file: 87028-22-6.mol

Synonyms:29-fluorostigmasterol

Chemical Property of 29-Fluorostigmasterol

Chemical Property:

• Vapor Pressure: 1.48E-12mmHg at 25°C
• Boiling Point: 510.4°Cat760mmHg
• Flash Point: 323.4°C
• PSA: 20.23000
• Density: 1.01g/cm³
• LogP: 7.75040
• XLogP3: 8.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 430.36109428
• Heavy Atom Count: 31
• Complexity: 695

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(CCF)C=CC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
• Isomeric SMILES: C[C@H](/C=C/[C@@H](CCF)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C

Technology Process of 29-Fluorostigmasterol

There total 5 articles about 29-Fluorostigmasterol 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: 75.0%

(1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-6-[(E)-(1R,4S)-4-(2-Fluoro-ethyl)-1,5-dimethyl-hex-2-enyl]-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene (87004-52-2) → 29-Fluorostigmasterol (87028-22-6)

Guidance literature:

With toluene-4-sulfonic acid; In 1,4-dioxane; water; Heating;

DOI:10.1016/S0040-4039(00)81955-3

Reference yield:

(20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde (25819-77-6) → 29-Fluorostigmasterol (87028-22-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) LDA / 1.) THF, -78 deg C

2: 86 percent / 2,4,6-Trimethylbenzoic acid / xylene / 140 °C

3: 90 percent / LiAlH₄ / tetrahydrofuran

4: 63 percent / Diethylaminosulfur trifluoride, CaCO₃ / CH₂Cl₂ / -78 - 25 °C

5: 75 percent / p-TsOH / dioxane; H₂O / Heating

With lithium aluminium tetrahydride; diethylamino-sulfur trifluoride; toluene-4-sulfonic acid; calcium carbonate; lithium diisopropyl amide; mesitylenecarboxylic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; xylene;

DOI:10.1016/S0040-4039(00)81955-3

Reference yield:

(22R)-6-β-methoxy-3α,5-cyclo-5α-cholest-23-yn-22-ol (71417-27-1) → 29-Fluorostigmasterol (87028-22-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / 2,4,6-Trimethylbenzoic acid / xylene / 140 °C

2: 90 percent / LiAlH₄ / tetrahydrofuran

3: 63 percent / Diethylaminosulfur trifluoride, CaCO₃ / CH₂Cl₂ / -78 - 25 °C

4: 75 percent / p-TsOH / dioxane; H₂O / Heating

With lithium aluminium tetrahydride; diethylamino-sulfur trifluoride; toluene-4-sulfonic acid; calcium carbonate; mesitylenecarboxylic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; xylene;

DOI:10.1016/S0040-4039(00)81955-3

upstream raw materials:

(1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-6-[(E)-(1R,4S)-4-(2-Fluoro-ethyl)-1,5-dimethyl-hex-2-enyl]-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene

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

(22R)-6-β-methoxy-3α,5-cyclo-5α-cholest-23-yn-22-ol

(E)-(3S,6R)-3-Isopropyl-6-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-hept-4-en-1-ol