3-Hydroxy-5-oxo-ophiobola-7,19-dien-25-al

Base Information

• Chemical Name: 3-Hydroxy-5-oxo-ophiobola-7,19-dien-25-al
• CAS No.: 19022-51-6
• Molecular Formula: C₂₅H₃₈O₃
• Molecular Weight: 386.575
• Mol file: 19022-51-6.mol

Synonyms:3-hydroxy-5-oxo-ophiobola-7,19-dien-25-al;ophiobolin C

Chemical Property of 3-Hydroxy-5-oxo-ophiobola-7,19-dien-25-al

Chemical Property:

• Vapor Pressure: 1.21E-12mmHg at 25°C
• Boiling Point: 512.4°Cat760mmHg
• Flash Point: 277.8°C
• PSA: 54.37000
• Density: 1.064g/cm³
• LogP: 5.27670
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 386.28209507
• Heavy Atom Count: 28
• Complexity: 686

Purity/Quality:

>98% by HPLC ^*data from raw suppliers

Ophiobolin C ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC=C(C)C)C1CCC2(C1CC=C(C3C(C2)C(CC3=O)(C)O)C=O)C
• Isomeric SMILES: CC(CCC=C(C)C)[C@H]1CC[C@]2([C@H]1C/C=C(\[C@@H]3[C@H](C2)[C@@](CC3=O)(C)O)/C=O)C
• Description: Ophiobolin C is a sesterterpenoid fungal phytoxin produced by many species of the genus Bipolaris. It has been identified as an antagonist of chemokine receptor CCR5 binding (IC50 = 40 μM) to the envelope protein gp120 and to CD4, which is known to mediate HIV-1 viral entry into cells. Ophiobolin C is also reported to be cytotoxic to chronic lymphocytic leukemia cells (LC50 = 8 nM).
• Uses: Ophiobolin C is a member of the ophiobolin class of phytotoxic metabolites produced by many species of the genus Bipolaris. Ophiobolin C inhibits human CCR5 binding to the envelope protein gp120 and CD4 that mediates HIV-1 entry into cells. Blockade of this binding was considered by scientists at Merck as a potential new mode of action for the treatment of HIV-1 infection. Ophiobolin C is an inhibitor of human CCR5 binding to HIV-1 gp120.

Technology Process of 3-Hydroxy-5-oxo-ophiobola-7,19-dien-25-al

There total 26 articles about 3-Hydroxy-5-oxo-ophiobola-7,19-dien-25-al 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:

{(1S,2S,3R)-3-((S)-4-Benzyloxy-1-methyl-butyl)-1-methyl-2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopentylmethoxy}-tert-butyl-diphenyl-silane (119619-00-0) → Ophiobolin C (6589-06-6,19022-51-6)

Guidance literature:

Multi-step reaction with 19 steps

1: H₂ / Pd(OH)2 / ethanol / 760 Torr / Ambient temperature

2: pyridine / Ambient temperature

3: n-Bu₄NF / dimethylformamide / 50 °C

4: Swern oxidation

5: 2.) Et₃N, DMAP / 1.) Et₂O, -78 deg C, 2.) CH₂Cl₂

6: 90 percent / 48percent aq. HF / tetrahydrofuran / 0 deg C then room temp.

7: 1.) ICl, 2.) n-Bu₄NF, HF / 1.) CH₂Cl₂, -78 deg C then 0 deg C, 2.) THF, 0 deg C, 1 min

8: p-TsOH / CH₂Cl₂; methanol / Ambient temperature

9: Swern oxidation

10: 73 percent / CrCl₂, NiCl₂ / dimethylsulfoxide; various solvent(s) / 2 h / Ambient temperature

11: t-BuOOH, VO(acac)2 / benzene / Ambient temperature

12: pyridine, DMAP / CH₂Cl₂ / Ambient temperature

13: n-Bu₃SnH, AIBN / benzene / 0.05 h / Heating

14: imidazole / dimethylformamide / Ambient temperature

15: diethyl ether / 0 deg C then room temp.

16: Swern oxidation

17: tetrahydrofuran / -78 deg C then 0 deg C

18: n-Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

19: Swern oxidation

With pyridine; 1H-imidazole; chromium dichloride; tert.-butylhydroperoxide; dmap; bis(acetylacetonate)oxovanadium; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; Iodine monochloride; toluene-4-sulfonic acid; triethylamine; nickel dichloride; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00189a069

Reference yield:

{(1S,4S,5S)-4-((S)-4-Benzyloxy-1-methyl-butyl)-1-methyl-5-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopent-2-enylmethoxy}-tert-butyl-diphenyl-silane (119594-26-2) → Ophiobolin C (6589-06-6,19022-51-6)

Guidance literature:

Multi-step reaction with 20 steps

1: H₂ / PtO₂ / ethyl acetate / 760 Torr / Ambient temperature

2: H₂ / Pd(OH)2 / ethanol / 760 Torr / Ambient temperature

3: pyridine / Ambient temperature

4: n-Bu₄NF / dimethylformamide / 50 °C

5: Swern oxidation

6: 2.) Et₃N, DMAP / 1.) Et₂O, -78 deg C, 2.) CH₂Cl₂

7: 90 percent / 48percent aq. HF / tetrahydrofuran / 0 deg C then room temp.

8: 1.) ICl, 2.) n-Bu₄NF, HF / 1.) CH₂Cl₂, -78 deg C then 0 deg C, 2.) THF, 0 deg C, 1 min

9: p-TsOH / CH₂Cl₂; methanol / Ambient temperature

10: Swern oxidation

11: 73 percent / CrCl₂, NiCl₂ / dimethylsulfoxide; various solvent(s) / 2 h / Ambient temperature

12: t-BuOOH, VO(acac)2 / benzene / Ambient temperature

13: pyridine, DMAP / CH₂Cl₂ / Ambient temperature

14: n-Bu₃SnH, AIBN / benzene / 0.05 h / Heating

15: imidazole / dimethylformamide / Ambient temperature

16: diethyl ether / 0 deg C then room temp.

17: Swern oxidation

18: tetrahydrofuran / -78 deg C then 0 deg C

19: n-Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

20: Swern oxidation

With pyridine; 1H-imidazole; chromium dichloride; tert.-butylhydroperoxide; dmap; bis(acetylacetonate)oxovanadium; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; Iodine monochloride; toluene-4-sulfonic acid; triethylamine; nickel dichloride; platinum(IV) oxide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00189a069

Reference yield:

(S)-5-Benzyloxy-2-{(1S,4S,5S)-4-(tert-butyl-diphenyl-silanyloxymethyl)-4-methyl-5-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopent-2-enyl}-pentan-1-ol (119594-24-0) → Ophiobolin C (6589-06-6,19022-51-6)

Guidance literature:

Multi-step reaction with 22 steps

1: Et₃N / CH₂Cl₂ / 0 °C

2: LiAlH₄ / diethyl ether / Ambient temperature

3: H₂ / PtO₂ / ethyl acetate / 760 Torr / Ambient temperature

4: H₂ / Pd(OH)2 / ethanol / 760 Torr / Ambient temperature

5: pyridine / Ambient temperature

6: n-Bu₄NF / dimethylformamide / 50 °C

7: Swern oxidation

8: 2.) Et₃N, DMAP / 1.) Et₂O, -78 deg C, 2.) CH₂Cl₂

9: 90 percent / 48percent aq. HF / tetrahydrofuran / 0 deg C then room temp.

10: 1.) ICl, 2.) n-Bu₄NF, HF / 1.) CH₂Cl₂, -78 deg C then 0 deg C, 2.) THF, 0 deg C, 1 min

11: p-TsOH / CH₂Cl₂; methanol / Ambient temperature

12: Swern oxidation

13: 73 percent / CrCl₂, NiCl₂ / dimethylsulfoxide; various solvent(s) / 2 h / Ambient temperature

14: t-BuOOH, VO(acac)2 / benzene / Ambient temperature

15: pyridine, DMAP / CH₂Cl₂ / Ambient temperature

16: n-Bu₃SnH, AIBN / benzene / 0.05 h / Heating

17: imidazole / dimethylformamide / Ambient temperature

18: diethyl ether / 0 deg C then room temp.

19: Swern oxidation

20: tetrahydrofuran / -78 deg C then 0 deg C

21: n-Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

22: Swern oxidation

With pyridine; 1H-imidazole; chromium dichloride; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; bis(acetylacetonate)oxovanadium; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; Iodine monochloride; toluene-4-sulfonic acid; triethylamine; nickel dichloride; platinum(IV) oxide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00189a069

upstream raw materials:

(E)-(1R,3R,3aS,6aS,7R,9aR,10aS)-7-((S)-1,5-Dimethyl-hex-4-enyl)-4-hydroxymethyl-1,9a-dimethyl-1,2,3,3a,6,6a,7,8,9,9a,10,10a-dodecahydro-dicyclopenta[a,d]cyclooctene-1,3-diol

2,2-Dimethyl-propionic acid (S)-4-{(1R,2S,3S)-3-hydroxymethyl-3-methyl-2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopentyl}-pentyl ester

2,2-Dimethyl-propionic acid (S)-4-{(1R,2S,3S)-3-formyl-3-methyl-2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopentyl}-pentyl ester

(S)-4-{(1R,2S,3S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-3-methyl-2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-cyclopentyl}-pentan-1-ol