Verrucosidin

Base Information

• Chemical Name: Verrucosidin
• CAS No.: 88389-71-3
• Molecular Formula: C₂₄H₃₂O₆
• Molecular Weight: 416.514
• DSSTox Substance ID: DTXSID701045464
• Nikkaji Number: J168.844H
• Wikipedia: Verrucosidin
• Wikidata: Q15427942
• Metabolomics Workbench ID: 141122
• ChEMBL ID: CHEMBL512656
• Mol file: 88389-71-3.mol

Synonyms:verrucosidin

Chemical Property of Verrucosidin

Chemical Property:

• Vapor Pressure: 1.06E-12mmHg at 25°C
• Boiling Point: 563.1°C at 760 mmHg
• Flash Point: 242.7°C
• PSA: 73.73000
• Density: 1.19g/cm³
• LogP: 4.10670
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 416.21988874
• Heavy Atom Count: 30
• Complexity: 939

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2(C(O2)C(O1)(C)C=C(C)C=C(C)C3C(O3)(C)C4=C(C(=C(C(=O)O4)C)OC)C)C
• Isomeric SMILES: C[C@@H]1[C@@]2([C@@H](O2)[C@](O1)(C)/C=C(\C)/C=C(\C)/[C@H]3[C@](O3)(C)C4=C(C(=C(C(=O)O4)C)OC)C)C

Technology Process of Verrucosidin

There total 54 articles about Verrucosidin 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:

(2E,5E)-3,5-dimethylhepta-2,5-dien-4-ol (49587-60-2) → verrucosidin (88389-71-3)

Guidance literature:

Multi-step reaction with 24 steps

1: 74 percent / Ti(O-i-Pr)4, L(+)DIPT, t-BuOOH / CH₂Cl₂ / -40 °C

2: 88 percent / NaH, n-Bu₄NI / dimethylformamide

3: OsO₄, N-methylmorpholine N-oxide / acetone; H₂O / 0 °C

4: 88 percent / pyridine

5: hydrogen / 20percent Pd(OH)2/C / ethanol

6: SnCl₄ / CH₂Cl₂ / -50 °C

7: K₂CO₃ / methanol

8: D-10-camphorsulfonic acid / acetone / Heating

9: pyridine / DMAP

10: DBU / toluene / 200 °C

11: 1) O₃, Me₂S / 1) CH₂Cl₂, -78 deg C

12: AcOH / H₂O / Heating

13: SO₃, pyridine, Et₃N / dimethylsulfoxide; CH₂Cl₂

14: NaBH₄ / tetrahydrofuran / -78 - -30 °C

15: pyridine / DMAP

16: NaOEt / ethanol

17: DIBAH / CH₂Cl₂ / -78 °C

18: MnO₂ / CH₂Cl₂

19: 60 percent / lithium hexamethyldisilazide / tetrahydrofuran / 0.17 h / -78 °C

20: pyridine / DMAP / CH₂Cl₂

21: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂

22: CsF / ethanol

23: 1) NaBH₄, CeCl₃; 2) MsCl, pyridine / 2) DMAP / 1) MeOH, -30 deg C

24: 1) 1 N H₂SO₄; 2) MsCl / 2) DMAP / 1) THF; 2) CH₂Cl₂

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; manganese(IV) oxide; sodium tetrahydroborate; osmium(VIII) oxide; cerium(III) chloride; dimethylsulfide; L-(+)-diisopropyl tartrate; sulfuric acid; sulfur trioxide; hydrogen; sodium ethanolate; tin(IV) chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ozone; acetic acid; methanesulfonyl chloride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; cesium fluoride; lithium hexamethyldisilazane; dmap; palladium dihydroxide; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/ja00223a055

Reference yield:

(E)-2-Methyl-3-((1S,2S,4R,5R)-2,4,5-trimethyl-3,6-dioxa-bicyclo[3.1.0]hex-2-yl)-propenal (115186-64-6) → verrucosidin (88389-71-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 60 percent / lithium hexamethyldisilazide / tetrahydrofuran / 0.17 h / -78 °C

2: pyridine / DMAP / CH₂Cl₂

3: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂

4: CsF / ethanol

5: 1) NaBH₄, CeCl₃; 2) MsCl, pyridine / 2) DMAP / 1) MeOH, -30 deg C

6: 1) 1 N H₂SO₄; 2) MsCl / 2) DMAP / 1) THF; 2) CH₂Cl₂

With pyridine; sodium tetrahydroborate; cerium(III) chloride; sulfuric acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; cesium fluoride; lithium hexamethyldisilazane; dmap; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/ja00223a055

Reference yield:

(E)-2-Methyl-3-((1S,2S,4R,5R)-2,4,5-trimethyl-3,6-dioxa-bicyclo[3.1.0]hex-2-yl)-acrylic acid ethyl ester (115186-63-5) → verrucosidin (88389-71-3)

Guidance literature:

Multi-step reaction with 8 steps

1: DIBAH / CH₂Cl₂ / -78 °C

2: MnO₂ / CH₂Cl₂

3: 60 percent / lithium hexamethyldisilazide / tetrahydrofuran / 0.17 h / -78 °C

4: pyridine / DMAP / CH₂Cl₂

5: 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂

6: CsF / ethanol

7: 1) NaBH₄, CeCl₃; 2) MsCl, pyridine / 2) DMAP / 1) MeOH, -30 deg C

8: 1) 1 N H₂SO₄; 2) MsCl / 2) DMAP / 1) THF; 2) CH₂Cl₂

With pyridine; manganese(IV) oxide; sodium tetrahydroborate; cerium(III) chloride; sulfuric acid; diisobutylaluminium hydride; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; cesium fluoride; lithium hexamethyldisilazane; dmap; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/ja00223a055

upstream raw materials:

6-[(3E,5E)-(S)-1-Hydroxy-1,3,5-trimethyl-2-oxo-6-((1S,2S,4R,5R)-2,4,5-trimethyl-3,6-dioxa-bicyclo[3.1.0]hex-2-yl)-hexa-3,5-dienyl]-4-methoxy-3,5-dimethyl-pyran-2-one

6-[(3E,5E)-(R)-1,2-Dihydroxy-1,3,5-trimethyl-6-((1S,2S,4R,5R)-2,4,5-trimethyl-3,6-dioxa-bicyclo[3.1.0]hex-2-yl)-hexa-3,5-dienyl]-4-methoxy-3,5-dimethyl-pyran-2-one

(2E,5E)-3,5-dimethylhepta-2,5-dien-4-ol

(E)-2-Methyl-3-((1S,2S,4R,5R)-2,4,5-trimethyl-3,6-dioxa-bicyclo[3.1.0]hex-2-yl)-propenal