(2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-5-methoxy-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracene-1,11-dione

Base Information

Chemical Name:(2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-5-methoxy-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracene-1,11-dione
CAS No.:149400-21-5
Molecular Formula:C₃₇H₅₀O₆Si
Molecular Weight:618.886
Hs Code.:

(2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-5-methoxy-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracene-1,11-dione

Synonyms:(2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-5-methoxy-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracene-1,11-dione

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Chemical Property of (2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-5-methoxy-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracene-1,11-dione

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Technology Process of (2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-5-methoxy-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracene-1,11-dione

There total 27 articles about (2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-5-methoxy-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracene-1,11-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: 95.0%

: 149400-44-2
Acetic acid (2R,3R,3aS,5S,6aR,7aS,8R,11aS,11bS,11cS)-11c-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-3,8,11a-trimethyl-1,11-dioxo-hexadecahydro-6-oxa-benzo[de]anthracen-2-yl ester

: 149400-21-5
(+)-(12α,16β)-20-(tert-butyldiphenylsiloxy)-12-hydroxy-16-methoxypicrasane-1,11-dione

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 3h;
DOI:10.1021/ja00067a025

Reference yield:

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

: 149400-21-5
(2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-5-methoxy-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracene-1,11-dione

Guidance literature:: Multi-step reaction with 17 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

With pyridine; 1H-imidazole; hydrogenchloride; 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; pyridinium chlorochromate; diborane; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 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

: 149400-21-5
(2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-5-methoxy-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracene-1,11-dione

Guidance literature:: Multi-step reaction with 17 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

With pyridine; 1H-imidazole; hydrogenchloride; 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; pyridinium chlorochromate; diborane; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja00181a079