(+)-(1β,12α,15β,16α)-20-(tert-butyldiphenylsiloxy)-15,16-dihydroxy-1-methoxy-12-(methoxymethoxy)picrasane-2,11-dione

Base Information

Chemical Name:(+)-(1β,12α,15β,16α)-20-(tert-butyldiphenylsiloxy)-15,16-dihydroxy-1-methoxy-12-(methoxymethoxy)picrasane-2,11-dione
CAS No.:149400-30-6
Molecular Formula:C₃₉H₅₄O₉Si
Molecular Weight:694.938
Hs Code.:

Synonyms:(+)-(1β,12α,15β,16α)-20-(tert-butyldiphenylsiloxy)-15,16-dihydroxy-1-methoxy-12-(methoxymethoxy)picrasane-2,11-dione

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Chemical Property of (+)-(1β,12α,15β,16α)-20-(tert-butyldiphenylsiloxy)-15,16-dihydroxy-1-methoxy-12-(methoxymethoxy)picrasane-2,11-dione

Chemical Property:

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Technology Process of (+)-(1β,12α,15β,16α)-20-(tert-butyldiphenylsiloxy)-15,16-dihydroxy-1-methoxy-12-(methoxymethoxy)picrasane-2,11-dione

There total 24 articles about (+)-(1β,12α,15β,16α)-20-(tert-butyldiphenylsiloxy)-15,16-dihydroxy-1-methoxy-12-(methoxymethoxy)picrasane-2,11-dione 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: 85.0%

: 149400-28-2
(-)-(1β,12α)-20-(tert-butyldiphenylsiloxy)-1-methoxy-12-(methoxymethoxy)picras-15-ene-2,11-dione

: 149400-30-6
(+)-(1β,12α,15β,16α)-20-(tert-butyldiphenylsiloxy)-15,16-dihydroxy-1-methoxy-12-(methoxymethoxy)picrasane-2,11-dione

: (+)-(1β,12α,15β,16β)-20-(tert-butyldiphenylsiloxy)-15,16-dihydroxy-1-methoxy-12-(methoxymethoxy)picrasane-2,11-dione

Guidance literature:: With pyridine; osmium(VIII) oxide; sodium hydrogensulfite; Yield given. Multistep reaction; 1.) 1 h, 2.) 2 h;
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

: 149400-30-6
(+)-(1β,12α,15β,16α)-20-(tert-butyldiphenylsiloxy)-15,16-dihydroxy-1-methoxy-12-(methoxymethoxy)picrasane-2,11-dione

Guidance literature:: Multi-step reaction with 12 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

With pyridine; chromium(VI) oxide; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; osmium(VIII) oxide; Celite; dihydrogen peroxide; sodium acetate; pyridinium p-toluenesulfonate; sodium hydrogensulfite; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; diborane; lithium hexamethyldisilazane; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/ja00067a025

Reference yield:

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

: 149400-30-6
(+)-(1β,12α,15β,16α)-20-(tert-butyldiphenylsiloxy)-15,16-dihydroxy-1-methoxy-12-(methoxymethoxy)picrasane-2,11-dione

Guidance literature:: Multi-step reaction with 13 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

With pyridine; chromium(VI) oxide; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; osmium(VIII) oxide; Celite; dihydrogen peroxide; sodium acetate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogensulfite; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; diborane; lithium hexamethyldisilazane; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; toluene;
DOI:10.1021/ja00067a025