(+)-<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

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Chemical Name:(+)-<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
CAS No.:149400-35-1
Molecular Formula:C₄₄H₅₈O₁₁Si
Molecular Weight:791.023
Hs Code.:

Synonyms:(+)-<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

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Chemical Property of (+)-<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

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Technology Process of (+)-<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

There total 22 articles about (+)-<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 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%

: 149400-33-9
(+)-(1β,12α,15β)-20-(tert-butyldiphenylsiloxy)-15-hydroxy-1-methoxy-12-(methoxymethoxy)picras-3-ene-2,11,16-trione

: 149312-29-8
(S)-(-)-5-ethyl-5-methyl-1,3-dioxolane-2,4-dione

: 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

Guidance literature:: With dmap; In dichloromethane; for 8h; 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

: 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

Guidance literature:: Multi-step reaction with 19 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

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; 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:

: 149400-08-8
(-)-(1β)-20-(tert-butyldiphenylsiloxy)-1-hydroxypicras-11-en-16-one

: 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

Guidance literature:: Multi-step reaction with 20 steps

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

2: pyridinium p-toluenesulfonate / tetrahydrofuran / 12 h

3: 100 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / a) 0 deg C, 1 h, b) RT, 45 min

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

5: 96 percent / pyridine, CrO₃, Celite / CH₂Cl₂ / 5.17 h / 0 - 20 °C

6: 95 percent / 1.5 N aq. NaOH / tetrahydrofuran; methanol / 3 h / 0 - 20 °C

7: 89 percent / N,N-diisopropylethylamine / 1,2-dichloro-ethane / 24 h / Ambient temperature

8: 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

9: 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

10: 94 percent / Celite, sodium acetate, pyridinium chlorochromate / CH₂Cl₂ / a) 0 deg C, 20 min, b) RT, 2 h 15 min

11: 91 percent / 10percent aq. HCl / tetrahydrofuran / 24 h / Ambient temperature

12: 96 percent / pyridine, POCl₃ / 1 h / 80 °C

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

14: 87 percent / 1-hydroxy-1,3-dihydro-3,3-bis(trifluoromethyl)-1,2-benziodoxole 1-oxide / CH₂Cl₂ / 1 h / Ambient temperature

15: 82 percent / 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 0.33 h / Ambient temperature

16: 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

17: N-bromosuccinimide / tetrahydrofuran / 0.17 h

18: 93 percent / Li₂CO₃, LiBr / dimethylformamide / 0.75 h / 120 °C

19: 100 percent / 10percent aq. HCl / tetrahydrofuran / 0.5 h / 0 °C

20: 92 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 8 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; dihydrogen peroxide; sodium acetate; pyridinium p-toluenesulfonate; 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; toluene;
DOI:10.1021/ja00067a025