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

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Chemical Name:(+)-<1β,12α,15β(S)>-20-(tert-butyldiphenylsiloxy)-1,12-dihydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy)picras-3-ene-2,11,16-trione
CAS No.:149400-36-2
Molecular Formula:C₄₁H₅₂O₁₀Si
Molecular Weight:732.943
Hs Code.:

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

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

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

There total 25 articles about (+)-<1β,12α,15β(S)>-20-(tert-butyldiphenylsiloxy)-1,12-dihydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy)picras-3-ene-2,11,16-trione 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: 61.0%

: 149400-35-1
(+)-<1β,12α,15β(S)>-20-(tert-butyldiphenylsiloxy)-15-(2-hydroxy-2-methyl-1-oxobutoxy)-1-methoxy-12-(methoxymethoxy)picras-3-ene-2,11,16-trione

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

Guidance literature:: With boron tribromide; In dichloromethane; a) -78 deg C, 65 min, b) from -78 deg C to -23 deg C, 40 min;
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

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

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: 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

With pyridine; chromium(VI) oxide; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; N-Bromosuccinimide; osmium(VIII) oxide; Celite; 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:

: 149400-12-4
(+)-(1β,16β)-20-(tert-butyldiphenylsiloxy)-1,16-dimethoxypicras-11-ene

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

Guidance literature:: Multi-step reaction with 23 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

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; 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