[(1S,5R,6R,7S,8R,11R,13S,17S,18S,19R)-4,5,17-Trihydroxy-6,14,18-trimethyl-9,16-dioxo-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-en-8-yl] (2S)-2-hydroxy-2-methylbutanoate

Base Information

• Chemical Name: [(1S,5R,6R,7S,8R,11R,13S,17S,18S,19R)-4,5,17-Trihydroxy-6,14,18-trimethyl-9,16-dioxo-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-en-8-yl] (2S)-2-hydroxy-2-methylbutanoate
• CAS No.: 1259-86-5
• Molecular Formula: C₂₅H₃₄O₁₀
• Molecular Weight: 494.539

Synonyms:glaucarubinone

Chemical Property of [(1S,5R,6R,7S,8R,11R,13S,17S,18S,19R)-4,5,17-Trihydroxy-6,14,18-trimethyl-9,16-dioxo-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-en-8-yl] (2S)-2-hydroxy-2-methylbutanoate

Chemical Property:

• Vapor Pressure: 1.47E-23mmHg at 25°C
• Boiling Point: 714.1°Cat760mmHg
• Flash Point: 240.7°C
• PSA: 159.82000
• Density: 1.44g/cm³
• LogP: -0.15110
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 494.21519728
• Heavy Atom Count: 35
• Complexity: 1020

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)(C(=O)OC1C2C(C(C3(C4C2(CO3)C(CC5C4(C(C(=O)C=C5C)O)C)OC1=O)O)O)C)O
• Isomeric SMILES: CC[C@@](C)(C(=O)O[C@@H]1[C@H]2[C@H]([C@H](C3([C@H]4[C@@]2(CO3)[C@@H](C[C@@H]5[C@@]4([C@@H](C(=O)C=C5C)O)C)OC1=O)O)O)C)O

Technology Process of [(1S,5R,6R,7S,8R,11R,13S,17S,18S,19R)-4,5,17-Trihydroxy-6,14,18-trimethyl-9,16-dioxo-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-en-8-yl] (2S)-2-hydroxy-2-methylbutanoate

There total 26 articles about [(1S,5R,6R,7S,8R,11R,13S,17S,18S,19R)-4,5,17-Trihydroxy-6,14,18-trimethyl-9,16-dioxo-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-en-8-yl] (2S)-2-hydroxy-2-methylbutanoate 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: 56.0%

(+)-<1β,12α,15β(S)>-20-(tert-butyldiphenylsiloxy)-1,12-dihydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy)picras-3-ene-2,11,16-trione (149400-36-2) → glaucarubinone (1259-86-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.5h; Ambient temperature;

DOI:10.1021/ja00067a025

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 → glaucarubinone (1259-86-5)

Guidance literature:

Multi-step reaction with 21 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: 92 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 8 h / Ambient temperature

20: 61 percent / BBr₃ / CH₂Cl₂ / a) -78 deg C, 65 min, b) from -78 deg C to -23 deg C, 40 min

21: 56 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

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

Reference yield:

(+)-(1β,16β)-20-(tert-butyldiphenylsiloxy)-1,16-dimethoxypicras-11-ene (149400-12-4) → glaucarubinone (1259-86-5)

Guidance literature:

Multi-step reaction with 24 steps

1: 90 percent / CrO₃, aq. H₂SO₄ / acetone / 4.25 h / 0 - 20 °C

2: 67 percent / BF₃*Et₂O / various solvent(s) / 36 h / Ambient temperature

3: diisobutylaluminum hydride / tetrahydrofuran; toluene / 2.25 h / -78 °C

4: pyridinium p-toluenesulfonate / tetrahydrofuran / 12 h

5: 100 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / a) 0 deg C, 1 h, b) RT, 45 min

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

7: 96 percent / pyridine, CrO₃, Celite / CH₂Cl₂ / 5.17 h / 0 - 20 °C

8: 95 percent / 1.5 N aq. NaOH / tetrahydrofuran; methanol / 3 h / 0 - 20 °C

9: 89 percent / N,N-diisopropylethylamine / 1,2-dichloro-ethane / 24 h / Ambient temperature

10: 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

11: 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

12: 94 percent / Celite, sodium acetate, pyridinium chlorochromate / CH₂Cl₂ / a) 0 deg C, 20 min, b) RT, 2 h 15 min

13: 91 percent / 10percent aq. HCl / tetrahydrofuran / 24 h / Ambient temperature

14: 96 percent / pyridine, POCl₃ / 1 h / 80 °C

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

16: 87 percent / 1-hydroxy-1,3-dihydro-3,3-bis(trifluoromethyl)-1,2-benziodoxole 1-oxide / CH₂Cl₂ / 1 h / Ambient temperature

17: 82 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 0.33 h / Ambient temperature

18: 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

19: N-bromosuccinimide / tetrahydrofuran / 0.17 h

20: 93 percent / Li₂CO₃, LiBr / dimethylformamide / 0.75 h / 120 °C

21: 100 percent / 10percent aq. HCl / tetrahydrofuran / 0.5 h / 0 °C

22: 92 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 8 h / Ambient temperature

23: 61 percent / BBr₃ / CH₂Cl₂ / a) -78 deg C, 65 min, b) from -78 deg C to -23 deg C, 40 min

24: 56 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; chromium(VI) oxide; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; N-Bromosuccinimide; osmium(VIII) oxide; Celite; sulfuric acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium acetate; pyridinium p-toluenesulfonate; boron tribromide; lithium carbonate; diisobutylaluminium hydride; 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; acetone; toluene;

DOI:10.1021/ja00067a025

upstream raw materials:

(+)-<1β,12α,15β(S)>-20-(tert-butyldiphenylsiloxy)-1,12-dihydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy)picras-3-ene-2,11,16-trione

(+)-(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

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 1259-86-5 glaucarubinone

Send

Send

Metric Ton KG G Pound L ML

Send

Send