(2S,3aS,5aR,6R,7R,8aR,8bS)-2-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-decahydro-as-indacen-4-one

Base Information

• Chemical Name: (2S,3aS,5aR,6R,7R,8aR,8bS)-2-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-decahydro-as-indacen-4-one
• CAS No.: 188910-68-1
• Molecular Formula: C₄₄H₆₂O₅Si₂
• Molecular Weight: 727.144
• Mol file: 188910-68-1.mol

Synonyms:(2S,3aS,5aR,6R,7R,8aR,8bS)-2-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-decahydro-as-indacen-4-one

Chemical Property of (2S,3aS,5aR,6R,7R,8aR,8bS)-2-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-decahydro-as-indacen-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3aS,5aR,6R,7R,8aR,8bS)-2-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-decahydro-as-indacen-4-one

There total 20 articles about (2S,3aS,5aR,6R,7R,8aR,8bS)-2-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-decahydro-as-indacen-4-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: 86.0%

(2S,3aS,4S,5aR,6R,7R,8aS,8bS)-2-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-dodecahydro-as-indacen-4-ol (188910-83-0) → (2S,3aS,5aR,6R,7R,8aR,8bS)-2-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-decahydro-as-indacen-4-one (188910-68-1)

Guidance literature:

With pyridinium chlorochromate absorbed on neutral alumina; In dichloromethane; for 2h;

DOI:10.1021/ja974009l

Reference yield:

(+/-)-7,7-dimethoxynorbornen-2-one (64145-56-8) → (2S,3aS,5aR,6R,7R,8aR,8bS)-2-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-decahydro-as-indacen-4-one (188910-68-1)

Guidance literature:

Multi-step reaction with 16 steps

2: 1.) t-BuLi, 2.) CeCl₃

3: 77 percent / NaH / tetrahydrofuran / 2 h / Heating

4: DIBAL-H / hexane / 0.17 h / -78 °C

5: TsOH, H₂O / acetone

6: 71 percent / (i-Pr)2NEt / CH₂Cl₂ / 18 h

7: 78 percent / K₂CO₃ / methanol / 2 h / Heating

8: 62 percent / Li, NH₃ liq., t-BuOH / tetrahydrofuran / 4 h / 20 °C

9: 1.) NaH / 1.) THF, 20 min, 2.) THF, a) from 30 to 40 deg C, 1 h, b) reflux, 3 h

10: 93 percent / LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

11: 97 percent / LiAlH₄ / diethyl ether / 0.17 h / 0 °C

12: 1.) NaH / 1.) DMF, THF, -20 deg C, 15 min, 2.) DMF, THF, a) RT, overnight, b) 40 deg C, 2 h

13: 1.) LiBH₄, BF₃*THF, 2.) 3N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, from -30 to -20 deg C, 4.5 h, 2.) THF, RT, 1 h

14: 96 percent / imidazole, DMAP / CH₂Cl₂ / 0 °C

15: 51 percent / B-bromocatecholborane / CH₂Cl₂ / 0.25 h / -78 °C

16: 86 percent / PCC on alumina / CH₂Cl₂ / 2 h

With 1H-imidazole; dmap; sodium hydroxide; pyridinium chlorochromate absorbed on neutral alumina; lithium aluminium tetrahydride; lithium borohydride; cerium(III) chloride; boron trifluoride-tetrahydrofuran complex; bromocatecholborane; ammonia; water; dihydrogen peroxide; tert.-butyl lithium; lithium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone;

DOI:10.1021/ja974009l

Reference yield:

(R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone (61305-35-9) → (2S,3aS,5aR,6R,7R,8aR,8bS)-2-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-decahydro-as-indacen-4-one (188910-68-1)

Guidance literature:

Multi-step reaction with 17 steps

1: 1.) L-Selectride, Et₃N / 1.) THF, -78 deg C, 10 min, 2.) THF, RT, 3 h

2: 1.) Li₂CuCN(SnBu₃)2, 2.) Br₂ / 1.) THF, -78 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C

3: 1.) t-BuLi, 2.) CeCl₃

4: 77 percent / NaH / tetrahydrofuran / 2 h / Heating

5: DIBAL-H / hexane / 0.17 h / -78 °C

6: TsOH, H₂O / acetone

7: 71 percent / (i-Pr)2NEt / CH₂Cl₂ / 18 h

8: 78 percent / K₂CO₃ / methanol / 2 h / Heating

9: 62 percent / Li, NH₃ liq., t-BuOH / tetrahydrofuran / 4 h / 20 °C

10: 1.) NaH / 1.) THF, 20 min, 2.) THF, a) from 30 to 40 deg C, 1 h, b) reflux, 3 h

11: 93 percent / LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

12: 97 percent / LiAlH₄ / diethyl ether / 0.17 h / 0 °C

13: 1.) NaH / 1.) DMF, THF, -20 deg C, 15 min, 2.) DMF, THF, a) RT, overnight, b) 40 deg C, 2 h

14: 1.) LiBH₄, BF₃*THF, 2.) 3N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, from -30 to -20 deg C, 4.5 h, 2.) THF, RT, 1 h

15: 96 percent / imidazole, DMAP / CH₂Cl₂ / 0 °C

16: 51 percent / B-bromocatecholborane / CH₂Cl₂ / 0.25 h / -78 °C

17: 86 percent / PCC on alumina / CH₂Cl₂ / 2 h

With 1H-imidazole; dmap; sodium hydroxide; pyridinium chlorochromate absorbed on neutral alumina; lithium aluminium tetrahydride; lithium borohydride; cerium(III) chloride; boron trifluoride-tetrahydrofuran complex; Li₂CuCN(SnBu₃)2; bromocatecholborane; ammonia; water; dihydrogen peroxide; bromine; tert.-butyl lithium; lithium; L-Selectride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone;

DOI:10.1021/ja974009l

upstream raw materials:

(2S,3aS,4S,5aR,6R,7R,8aS,8bS)-2-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-dodecahydro-as-indacen-4-ol

(+/-)-7,7-dimethoxynorbornen-2-one

(R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone

p-methoxybenzyl chloride

Downstream raw materials:

(2S,3aR,5aR,6R,7R,8aR,8bS)-2-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-decahydro-as-indacen-4-one

2,2-Dimethyl-propionic acid (2R,3aS,5aR,6R,7R,8aS,8bR)-7-hydroxy-6-[2-(4-methoxy-benzyloxy)-ethyl]-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester

(2R,3aS,5aR,6R,7R,8aS,8bR)-7-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-ol

2,2-Dimethyl-propionic acid (2R,3aS,5aR,6R,7R,8aS,8bR)-7-(tert-butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester