Glaucarubolone

Base Information

• Chemical Name: Glaucarubolone
• CAS No.: 1990-01-8
• Molecular Formula: C₂₀H₂₆O₈
• Molecular Weight: 394.422
• NSC Number: 126764
• Nikkaji Number: J34.243B
• Wikidata: Q27106738
• NCI Thesaurus Code: C1114
• Metabolomics Workbench ID: 140912
• ChEMBL ID: CHEMBL510560
• Mol file: 1990-01-8.mol

Synonyms:glaucarubolone

Chemical Property of Glaucarubolone

Chemical Property:

• Vapor Pressure: 8.33E-20mmHg at 25°C
• Boiling Point: 652.8°Cat760mmHg
• Flash Point: 233.9°C
• PSA: 133.52000
• Density: 1.52g/cm³
• LogP: -0.86300
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 0
• Exact Mass: 394.16276778
• Heavy Atom Count: 28
• Complexity: 808

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2C(C(=O)OC3C24COC(C1O)(C4C5(C(C3)C(=CC(=O)C5O)C)C)O)O
• Isomeric SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)O[C@H]3[C@@]24CO[C@@]([C@@H]1O)([C@@H]4[C@@]5([C@@H](C3)C(=CC(=O)[C@H]5O)C)C)O)O

Technology Process of Glaucarubolone

There total 37 articles about Glaucarubolone 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: 92.0%

(+)-(1β,12α,15β)-20-(tert-butyldiphenylsiloxy)-1,12,15-trihydroxypicras-3-ene-2,11,16-trione → Glaucarubolon (1990-01-8,141762-82-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/ja00067a025

Reference yield: 92.0%

(2S,3S,3aR,4S,6aS,7aR,11R,11aR,11bS,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-2,4,11-trihydroxy-3,8,11a-trimethyl-2,3,3a,4,7,7a,11,11a,11b,11c-decahydro-6aH-6-oxa-benzo[de]anthracene-1,5,10-trione (141762-91-6) → (+/-)-glaucarubolone (1990-01-8,141762-82-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.333333h;

DOI:10.1016/S0040-4039(00)74149-9

Reference yield:

(3S,3aS,6aR,7aS,8R,11R,11aS,11bR,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracene-5,11-diol → Glaucarubolon (1990-01-8,141762-82-5)

Guidance literature:

Multi-step reaction with 20 steps

1: pyridinium p-toluenesulfonate / tetrahydrofuran / 12 h

2: 100 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / a) 0 deg C, 1 h, b) RT, 45 min

3: 1.) pyridine, OsO₄, 2.) aq. sodium bisulfite / 1.) from 0 deg C to RT, 25.5 h, 2.) 24 h

4: 96 percent / pyridine, CrO₃, Celite / CH₂Cl₂ / 5.17 h / 0 - 20 °C

5: 95 percent / 1.5 N aq. NaOH / tetrahydrofuran; methanol / 3 h / 0 - 20 °C

6: 89 percent / N,N-diisopropylethylamine / 1,2-dichloro-ethane / 24 h / Ambient temperature

7: 1.) hexamethylphosphoramide, lithium bis(trimethylsilyl)amide / 1.) THF, a) -78 deg C, 30 min, b) 0 deg C, 30 min, 2.) THF, a) -78 deg C, 5 min, b) 0 deg C, 45 min

8: 1.) diborane, 2.) 3N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, a) -23 deg C, 15 min, b) 0 deg C, 45 min, 2.) THF, RT, 1.5 h

9: 94 percent / Celite, sodium acetate, pyridinium chlorochromate / CH₂Cl₂ / a) 0 deg C, 20 min, b) RT, 2 h 15 min

10: 91 percent / 10percent aq. HCl / tetrahydrofuran / 24 h / Ambient temperature

11: 96 percent / pyridine, POCl₃ / 1 h / 80 °C

12: 1.) pyridine, OsO₄, 2.) aq. sodium bisulfite / 1.) 1 h, 2.) 2 h

13: 87 percent / 1-hydroxy-1,3-dihydro-3,3-bis(trifluoromethyl)-1,2-benziodoxole 1-oxide / CH₂Cl₂ / 1 h / Ambient temperature

14: 82 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 0.33 h / Ambient temperature

15: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 45 min, 2.) THF, a) -78 deg C, 15 min, b) 0 deg C, 5 min

16: N-bromosuccinimide / tetrahydrofuran / 0.17 h

17: 93 percent / Li₂CO₃, LiBr / dimethylformamide / 0.75 h / 120 °C

18: 100 percent / 10percent aq. HCl / tetrahydrofuran / 0.5 h / 0 °C

19: 84 percent / BBr₃ / CH₂Cl₂ / a) -78 deg C, 50 min, b) -23 deg C, 30 min

20: 92 percent / tetra-n-butylammonium fluoride / tetrahydrofuran

With pyridine; chromium(VI) oxide; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; N-Bromosuccinimide; osmium(VIII) oxide; Celite; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium acetate; pyridinium p-toluenesulfonate; boron tribromide; lithium carbonate; 1-hydroxy-1,3-dihydro-3,3-bis(trifluoromethyl)-1,2-benziodoxole 1-oxide; sodium hydrogensulfite; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium bromide; diborane; lithium hexamethyldisilazane; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00067a025

upstream raw materials:

(+)-(1β,16β)-20-(tert-butyldiphenylsiloxy)-1,16-dimethoxypicras-11-ene

(-)-(1β)-20-(tert-butyldiphenylsiloxy)-1-hydroxypicras-11-en-16-one

(-)-(1β)-20-(tert-butyldiphenylsiloxy)-1-methoxypicras-11-en-16-one

(+)-(1β,11α,12α,16β)-20-(tert-butyldiphenylsiloxy)-12-(acetyloxy)-16-methoxypicrasane-1,11-diol

Refernces

• 1、 Fleck,Grieco. "Synthetic studies on quassinoids: Total synthesis of (±)-glaucarubolone and (±)-holacanthone". . p. 1813 - 1816. Retrieved 2007/10/02.