6-Deoxocastasterone

Base Information

• Chemical Name: 6-Deoxocastasterone
• CAS No.: 87833-54-3
• Molecular Formula: C28H50O4
• Molecular Weight: 450.69
• DSSTox Substance ID: DTXSID6040951
• Metabolomics Workbench ID: 34790
• Nikkaji Number: J146.605D
• Wikidata: Q27109343
• Mol file: 87833-54-3.mol

Synonyms:6-deoxocastasterone

Chemical Property of 6-Deoxocastasterone

Chemical Property:

• Boiling Point: 568.1±25.0 °C(Predicted)
• PKA: 14.29±0.20(Predicted)
• PSA: 80.92000
• Density: 1.083±0.06 g/cm3(Predicted)
• LogP: 4.62700
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 450.37091007
• Heavy Atom Count: 32
• Complexity: 666

Purity/Quality:

95% ^*data from raw suppliers

6-Deoxocastasterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C)C(C(C(C)C1CCC2C1(CCC3C2CCC4C3(CC(C(C4)O)O)C)C)O)O
• Isomeric SMILES: C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(C[C@H]([C@H](C4)O)O)C)C)[C@H]([C@@H]([C@@H](C)C(C)C)O)O
• Uses: 6-Deoxocastasterone can be used for biological study for synergistic effect of auxins and brassinosteroids on the growth and regulation of metabolite content in Chlorella vulgaris.

Technology Process of 6-Deoxocastasterone

There total 18 articles about 6-Deoxocastasterone 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) → 6-deoxocastasterone (87833-54-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 61 percent / tetrahydrofuran / 1 h / Ambient temperature

2: 95 percent / propionic acid / xylene / 2 h / Heating

3: LiAlH₄ / tetrahydrofuran / 2 h / Heating

4: Et₃N / toluene / 2 h / Ambient temperature

5: LiAlH₄ / tetrahydrofuran / 2 h / Heating

6: 50 percent / potassium hexacyanoferrate(III), K₂CO₃, methanesulfonamide, dihydroquinidine p-chlorobenzoate, OsO₄ / H₂O; 2-methyl-propan-2-ol / 360 h / Ambient temperature

7: 99 percent / p-toluenesulfonic acid, H₂O / dioxane / 4 h / Heating

8: 99 percent / H₂ / 10percent Pd/C / ethanol / 2 h / 45 °C

9: p-toluenesulfonic acid / 1 h / Ambient temperature

10: pyridine / 1 h / Ambient temperature

11: 71 percent / Li₂CO₃ / dimethylformamide / 1 h / 170 °C

12: OsO₄, aq. THF, N-methylmorpholine N-oxide / 4 h / Ambient temperature

13: 1.) aq. AcOH, 2.) aq. KOH / 1.) 100 deg C, 3 h, 2.) MeOH, RT, 2 h

With tetrahydrofuran; pyridine; potassium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; dihydroquinidine 4-chlorobenzoate; methanesulfonamide; water; hydrogen; lithium carbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; propionic acid; 4-methylmorpholine N-oxide; triethylamine; potassium hexacyanoferrate(III); palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; toluene; xylene; tert-butyl alcohol;

Reference yield:

6-deoxoteasterone (85707-12-6) → 6-deoxocastasterone (87833-54-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / H₂ / 10percent Pd/C / ethanol / 2 h / 45 °C

2: p-toluenesulfonic acid / 1 h / Ambient temperature

3: pyridine / 1 h / Ambient temperature

4: 71 percent / Li₂CO₃ / dimethylformamide / 1 h / 170 °C

5: OsO₄, aq. THF, N-methylmorpholine N-oxide / 4 h / Ambient temperature

6: 1.) aq. AcOH, 2.) aq. KOH / 1.) 100 deg C, 3 h, 2.) MeOH, RT, 2 h

With tetrahydrofuran; pyridine; potassium hydroxide; osmium(VIII) oxide; hydrogen; lithium carbonate; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

Reference yield:

(22E)-6β-methoxy-3α,5-cyclo-24-α-methyl-5α-cholest-22-en-26-ol (189013-48-7) → 6-deoxocastasterone (87833-54-3)

Guidance literature:

Multi-step reaction with 10 steps

1: Et₃N / toluene / 2 h / Ambient temperature

2: LiAlH₄ / tetrahydrofuran / 2 h / Heating

3: 50 percent / potassium hexacyanoferrate(III), K₂CO₃, methanesulfonamide, dihydroquinidine p-chlorobenzoate, OsO₄ / H₂O; 2-methyl-propan-2-ol / 360 h / Ambient temperature

4: 99 percent / p-toluenesulfonic acid, H₂O / dioxane / 4 h / Heating

5: 99 percent / H₂ / 10percent Pd/C / ethanol / 2 h / 45 °C

6: p-toluenesulfonic acid / 1 h / Ambient temperature

7: pyridine / 1 h / Ambient temperature

8: 71 percent / Li₂CO₃ / dimethylformamide / 1 h / 170 °C

9: OsO₄, aq. THF, N-methylmorpholine N-oxide / 4 h / Ambient temperature

10: 1.) aq. AcOH, 2.) aq. KOH / 1.) 100 deg C, 3 h, 2.) MeOH, RT, 2 h

With tetrahydrofuran; pyridine; potassium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; dihydroquinidine 4-chlorobenzoate; methanesulfonamide; water; hydrogen; lithium carbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; triethylamine; potassium hexacyanoferrate(III); palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

upstream raw materials:

castasterone

6-deoxotyphasterol

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

6-deoxoteasterone