tert-Butyl-{(2S,3aS,4S,5aR,8aS,8bS)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methoxymethoxy-1,2,3,3a,4,5,5a,8,8a,8b-decahydro-as-indacen-2-yloxy}-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-{(2S,3aS,4S,5aR,8aS,8bS)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methoxymethoxy-1,2,3,3a,4,5,5a,8,8a,8b-decahydro-as-indacen-2-yloxy}-dimethyl-silane
• CAS No.: 188910-81-8
• Molecular Formula: C₃₀H₄₈O₅Si
• Molecular Weight: 516.794
• Mol file: 188910-81-8.mol

Synonyms:tert-Butyl-{(2S,3aS,4S,5aR,8aS,8bS)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methoxymethoxy-1,2,3,3a,4,5,5a,8,8a,8b-decahydro-as-indacen-2-yloxy}-dimethyl-silane

Chemical Property of tert-Butyl-{(2S,3aS,4S,5aR,8aS,8bS)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methoxymethoxy-1,2,3,3a,4,5,5a,8,8a,8b-decahydro-as-indacen-2-yloxy}-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-{(2S,3aS,4S,5aR,8aS,8bS)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methoxymethoxy-1,2,3,3a,4,5,5a,8,8a,8b-decahydro-as-indacen-2-yloxy}-dimethyl-silane

There total 14 articles about tert-Butyl-{(2S,3aS,4S,5aR,8aS,8bS)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methoxymethoxy-1,2,3,3a,4,5,5a,8,8a,8b-decahydro-as-indacen-2-yloxy}-dimethyl-silane 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:

(+/-)-7,7-dimethoxynorbornen-2-one (64145-56-8) → tert-Butyl-{(2S,3aS,4S,5aR,8aS,8bS)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methoxymethoxy-1,2,3,3a,4,5,5a,8,8a,8b-decahydro-as-indacen-2-yloxy}-dimethyl-silane (188910-81-8)

Guidance literature:

Multi-step reaction with 12 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

With lithium aluminium tetrahydride; cerium(III) chloride; ammonia; water; 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) → tert-Butyl-{(2S,3aS,4S,5aR,8aS,8bS)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methoxymethoxy-1,2,3,3a,4,5,5a,8,8a,8b-decahydro-as-indacen-2-yloxy}-dimethyl-silane (188910-81-8)

Guidance literature:

Multi-step reaction with 13 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

With lithium aluminium tetrahydride; cerium(III) chloride; Li₂CuCN(SnBu₃)2; ammonia; water; 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

Reference yield:

((S)-3-Bromo-cyclopent-3-enyloxy)-tert-butyl-dimethyl-silane (188910-40-9) → tert-Butyl-{(2S,3aS,4S,5aR,8aS,8bS)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-methoxymethoxy-1,2,3,3a,4,5,5a,8,8a,8b-decahydro-as-indacen-2-yloxy}-dimethyl-silane (188910-81-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) t-BuLi, 2.) CeCl₃

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

3: DIBAL-H / hexane / 0.17 h / -78 °C

4: TsOH, H₂O / acetone

5: 71 percent / (i-Pr)2NEt / CH₂Cl₂ / 18 h

6: 78 percent / K₂CO₃ / methanol / 2 h / Heating

7: 62 percent / Li, NH₃ liq., t-BuOH / tetrahydrofuran / 4 h / 20 °C

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

9: 93 percent / LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

10: 97 percent / LiAlH₄ / diethyl ether / 0.17 h / 0 °C

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

With lithium aluminium tetrahydride; cerium(III) chloride; ammonia; water; 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

upstream raw materials:

p-methoxybenzyl chloride

2-[(3aR,5S,5aS,7S,8aS,8bS)-7-(tert-Butyl-dimethyl-silanyloxy)-5-methoxymethoxy-1,3a,4,5,5a,6,7,8,8a,8b-decahydro-as-indacen-3-yl]-ethanol

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

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

Downstream raw materials:

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

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

(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

(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