(2R,3R,3aS,6aR,7aS,8S,11S,11aS,11bR,11cS)-9-Bromo-11c-(tert-butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-dodecahydro-6-oxa-benzo[de]anthracene-1,5,10-trione

Base Information

Chemical Name:(2R,3R,3aS,6aR,7aS,8S,11S,11aS,11bR,11cS)-9-Bromo-11c-(tert-butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-dodecahydro-6-oxa-benzo[de]anthracene-1,5,10-trione
CAS No.:149400-46-4
Molecular Formula:C₃₉H₅₁BrO₈Si
Molecular Weight:755.819
Hs Code.:

(2R,3R,3aS,6aR,7aS,8S,11S,11aS,11bR,11cS)-9-Bromo-11c-(tert-butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-dodecahydro-6-oxa-benzo[de]anthracene-1,5,10-trione

Synonyms:(2R,3R,3aS,6aR,7aS,8S,11S,11aS,11bR,11cS)-9-Bromo-11c-(tert-butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-dodecahydro-6-oxa-benzo[de]anthracene-1,5,10-trione

Suppliers and Price of (2R,3R,3aS,6aR,7aS,8S,11S,11aS,11bR,11cS)-9-Bromo-11c-(tert-butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-dodecahydro-6-oxa-benzo[de]anthracene-1,5,10-trione

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3R,3aS,6aR,7aS,8S,11S,11aS,11bR,11cS)-9-Bromo-11c-(tert-butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-dodecahydro-6-oxa-benzo[de]anthracene-1,5,10-trione

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (2R,3R,3aS,6aR,7aS,8S,11S,11aS,11bR,11cS)-9-Bromo-11c-(tert-butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-dodecahydro-6-oxa-benzo[de]anthracene-1,5,10-trione

There total 15 articles about (2R,3R,3aS,6aR,7aS,8S,11S,11aS,11bR,11cS)-9-Bromo-11c-(tert-butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-dodecahydro-6-oxa-benzo[de]anthracene-1,5,10-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:

: 149400-24-8
(-)-(1β,12α)-20-(tert-butyldiphenylsiloxy)-1-methoxy-12-(methoxymethoxy)picrasane-2,11,16-trione

: 149400-46-4
(2R,3R,3aS,6aR,7aS,8S,11S,11aS,11bR,11cS)-9-Bromo-11c-(tert-butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-dodecahydro-6-oxa-benzo[de]anthracene-1,5,10-trione

Guidance literature:: With camphor-10-sulfonic acid; pyridinium hydrobromide perbromide; In tetrahydrofuran; for 1h; 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

: 149400-46-4
(2R,3R,3aS,6aR,7aS,8S,11S,11aS,11bR,11cS)-9-Bromo-11c-(tert-butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-dodecahydro-6-oxa-benzo[de]anthracene-1,5,10-trione

Guidance literature:: Multi-step reaction with 11 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: 10percent aq. HCl / 14 h / Ambient temperature

10: 78 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

11: camphorsulfonic acid, pyridinium bromide perbromide / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; chromium(VI) oxide; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; osmium(VIII) oxide; Celite; camphor-10-sulfonic acid; dihydrogen peroxide; pyridinium hydrobromide perbromide; pyridinium p-toluenesulfonate; sodium hydrogensulfite; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; diborane; lithium hexamethyldisilazane; 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

: 149400-46-4
(2R,3R,3aS,6aR,7aS,8S,11S,11aS,11bR,11cS)-9-Bromo-11c-(tert-butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-dodecahydro-6-oxa-benzo[de]anthracene-1,5,10-trione

Guidance literature:: Multi-step reaction with 12 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: 10percent aq. HCl / 14 h / Ambient temperature

11: 78 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

12: camphorsulfonic acid, pyridinium bromide perbromide / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; chromium(VI) oxide; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; osmium(VIII) oxide; Celite; camphor-10-sulfonic acid; dihydrogen peroxide; pyridinium hydrobromide perbromide; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogensulfite; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; diborane; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; toluene;
DOI:10.1021/ja00067a025