(2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-2-methoxymethoxy-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,11a,11b,11c-dodecahydro-2H-6-oxa-benzo[de]anthracen-1-one

Base Information

Chemical Name:(2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-2-methoxymethoxy-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,11a,11b,11c-dodecahydro-2H-6-oxa-benzo[de]anthracen-1-one
CAS No.:149400-45-3
Molecular Formula:C₄₀H₅₆O₇Si
Molecular Weight:676.966
Hs Code.:

(2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-2-methoxymethoxy-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,11a,11b,11c-dodecahydro-2H-6-oxa-benzo[de]anthracen-1-one

Synonyms:(2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-2-methoxymethoxy-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,11a,11b,11c-dodecahydro-2H-6-oxa-benzo[de]anthracen-1-one

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Chemical Property of (2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-2-methoxymethoxy-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,11a,11b,11c-dodecahydro-2H-6-oxa-benzo[de]anthracen-1-one

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Technology Process of (2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-2-methoxymethoxy-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,11a,11b,11c-dodecahydro-2H-6-oxa-benzo[de]anthracen-1-one

There total 31 articles about (2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-2-methoxymethoxy-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,11a,11b,11c-dodecahydro-2H-6-oxa-benzo[de]anthracen-1-one 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:

: 95421-98-0
(E)-4-methyl-3,5-hexadienoic acid

: 149400-45-3
(2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-2-methoxymethoxy-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,11a,11b,11c-dodecahydro-2H-6-oxa-benzo[de]anthracen-1-one

Guidance literature:: Multi-step reaction with 19 steps

1: 72 percent / LiClO₄ / diethyl ether / 9 h / Ambient temperature

2: 1.) NaBH₄, 2.) concd. HCl / 1.) methanol, 0 deg C

3: 86 percent / imidazole / dimethylformamide

4: 100 percent / i-Bu₂AlH / tetrahydrofuran / -78 °C

5: 100 percent / concd. HCl / tetrahydrofuran

6: 1.) B₂H₆, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C

7: PCC, NaOAc / CH₂Cl₂

8: 1.) LDA / 1.) THF, from -78 deg C to 0 deg C, 2.) -78 deg C

9: Pd(OAc)2, Na₂CO₃ / acetonitrile / 45 °C

10: 81 percent / lithium, liquid ammonia, tert-butyl alcohol / -78 °C

11: methanol; tetrahydrofuran

12: n-butyllithium / -78 °C

14: 100 percent / Et₃N, DMAP / CH₂Cl₂

15: 83 percent / OsO₄, pyridine

16: Collins reagent

17: NaOH / methanol; tetrahydrofuran

18: i-Pr₂NEt / 1,2-dichloro-ethane

19: 1.) LiHMDS, HMPA / tetrahydrofuran

With pyridine; 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; palladium diacetate; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; Collins oxidation agent; ammonia; dihydrogen peroxide; sodium acetate; lithium perchlorate; lithium; diisobutylaluminium hydride; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; diborane; lithium hexamethyldisilazane; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja00181a079

Reference yield:

: 86669-09-2,87758-23-4,123929-85-1
(4aR,5S,8S,8aR)-8-Methoxy-5,8a-dimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbaldehyde

: 149400-45-3
(2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-2-methoxymethoxy-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,11a,11b,11c-dodecahydro-2H-6-oxa-benzo[de]anthracen-1-one

Guidance literature:: Multi-step reaction with 19 steps

1: 72 percent / LiClO₄ / diethyl ether / 9 h / Ambient temperature

2: 1.) NaBH₄, 2.) concd. HCl / 1.) methanol, 0 deg C

3: 86 percent / imidazole / dimethylformamide

4: 100 percent / i-Bu₂AlH / tetrahydrofuran / -78 °C

5: 100 percent / concd. HCl / tetrahydrofuran

6: 1.) B₂H₆, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C

7: PCC, NaOAc / CH₂Cl₂

8: 1.) LDA / 1.) THF, from -78 deg C to 0 deg C, 2.) -78 deg C

9: Pd(OAc)2, Na₂CO₃ / acetonitrile / 45 °C

10: 81 percent / lithium, liquid ammonia, tert-butyl alcohol / -78 °C

11: methanol; tetrahydrofuran

12: n-butyllithium / -78 °C

14: 100 percent / Et₃N, DMAP / CH₂Cl₂

15: 83 percent / OsO₄, pyridine

16: Collins reagent

17: NaOH / methanol; tetrahydrofuran

18: i-Pr₂NEt / 1,2-dichloro-ethane

19: 1.) LiHMDS, HMPA / tetrahydrofuran

With pyridine; 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; palladium diacetate; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; Collins oxidation agent; ammonia; dihydrogen peroxide; sodium acetate; lithium perchlorate; lithium; diisobutylaluminium hydride; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; diborane; lithium hexamethyldisilazane; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja00181a079

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

: 149400-45-3
(2R,3R,3aS,5S,6aR,7aS,8R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-2-methoxymethoxy-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,11a,11b,11c-dodecahydro-2H-6-oxa-benzo[de]anthracen-1-one

Guidance literature:: Multi-step reaction with 7 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

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