{(E)-(1R,2S,4S,8R)-1-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-2-methoxy-8-[(2R,4R)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4,6-dimethyl-undeca-6,10-dienyloxy}-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: {(E)-(1R,2S,4S,8R)-1-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-2-methoxy-8-[(2R,4R)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4,6-dimethyl-undeca-6,10-dienyloxy}-tert-butyl-dimethyl-silane
• CAS No.: 128461-64-3
• Molecular Formula: C₄₄H₇₀O₇Si
• Molecular Weight: 739.121

Synonyms:

Chemical Property of {(E)-(1R,2S,4S,8R)-1-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-2-methoxy-8-[(2R,4R)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4,6-dimethyl-undeca-6,10-dienyloxy}-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(E)-(1R,2S,4S,8R)-1-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-2-methoxy-8-[(2R,4R)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4,6-dimethyl-undeca-6,10-dienyloxy}-tert-butyl-dimethyl-silane

There total 26 articles about {(E)-(1R,2S,4S,8R)-1-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-2-methoxy-8-[(2R,4R)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4,6-dimethyl-undeca-6,10-dienyloxy}-tert-butyl-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:

benzyl bromide (100-39-0) → {(E)-(1R,2S,4S,8R)-1-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-2-methoxy-8-[(2R,4R)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4,6-dimethyl-undeca-6,10-dienyloxy}-tert-butyl-dimethyl-silane (128461-64-3)

Guidance literature:

Multi-step reaction with 16 steps

2: AcOH / tetrahydrofuran; H₂O / 50 °C

3: imidazole / dimethylformamide

4: 90 percent / t-BuOOH / (+)-DIPT, Ti(i-PrO)4 / CH₂Cl₂ / -20 °C

5: NaH / tetrahydrofuran / 0 °C

6: n-Bu₄NF / tetrahydrofuran

7: Dess-Martin periodinane reagent

8: tetrahydrofuran

9: H₂ / Pd/C / ethyl acetate

10: 1.) NaOH / 2.) CSA / 1.) EtOH, reflux; 2.) CH₂Cl₂

11: boron trifluoride etherate / 0 °C

12: 80 percent / sodium hexamethyldisilazide / tetrahydrofuran / -78 °C

13: 93 percent / LiAlH₄ / tetrahydrofuran / -20 °C

14: Et₃N / DMAP / CH₂Cl₂

15: 2,6-lutidine / CH₂Cl₂

16: LiEt₃BH / tetrahydrofuran

With 1H-imidazole; tert.-butylhydroperoxide; sodium hydroxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sodium hydride; lithium triethylborohydride; Dess-Martin periodane; acetic acid; triethylamine; 2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; palladium on activated charcoal; L-(+)-diisopropyl tartrate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)70631-9

Reference yield:

3-(p-methoxybenzyloxy)propanal (128461-65-4) → {(E)-(1R,2S,4S,8R)-1-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-2-methoxy-8-[(2R,4R)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4,6-dimethyl-undeca-6,10-dienyloxy}-tert-butyl-dimethyl-silane (128461-64-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) (c-C₅H₉)2OTf, i-Pr₂NEt / 2.) CH₂Cl₂, -78 deg C

2: 92 percent / DDQ / CH₂Cl₂

3: 1.) LiOH, H₂O₂; 2.) LiAlH₄ / 1.) THF, H₂O; 2.) THF, 0 deg C

4: (ClCO)2, Et₃N / dimethylsulfoxide; CH₂Cl₂ / -78 °C

5: tetrahydrofuran

7: 80 percent / sodium hexamethyldisilazide / tetrahydrofuran / -78 °C

8: 93 percent / LiAlH₄ / tetrahydrofuran / -20 °C

9: Et₃N / DMAP / CH₂Cl₂

10: 2,6-lutidine / CH₂Cl₂

11: LiEt₃BH / tetrahydrofuran

With lithium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; (c-C₅H₉)2OTf; dihydrogen peroxide; sodium hexamethyldisilazane; lithium triethylborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,6-dimethylpyridine; dmap; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)70631-9

Reference yield:

Propionic acid (R)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-allyl ester → {(E)-(1R,2S,4S,8R)-1-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-2-methoxy-8-[(2R,4R)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4,6-dimethyl-undeca-6,10-dienyloxy}-tert-butyl-dimethyl-silane (128461-64-3)

Guidance literature:

Multi-step reaction with 16 steps

2: AcOH / tetrahydrofuran; H₂O / 50 °C

3: imidazole / dimethylformamide

4: 90 percent / t-BuOOH / (+)-DIPT, Ti(i-PrO)4 / CH₂Cl₂ / -20 °C

5: NaH / tetrahydrofuran / 0 °C

6: n-Bu₄NF / tetrahydrofuran

7: Dess-Martin periodinane reagent

8: tetrahydrofuran

9: H₂ / Pd/C / ethyl acetate

10: 1.) NaOH / 2.) CSA / 1.) EtOH, reflux; 2.) CH₂Cl₂

11: boron trifluoride etherate / 0 °C

12: 80 percent / sodium hexamethyldisilazide / tetrahydrofuran / -78 °C

13: 93 percent / LiAlH₄ / tetrahydrofuran / -20 °C

14: Et₃N / DMAP / CH₂Cl₂

15: 2,6-lutidine / CH₂Cl₂

16: LiEt₃BH / tetrahydrofuran

With 1H-imidazole; tert.-butylhydroperoxide; sodium hydroxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sodium hydride; lithium triethylborohydride; Dess-Martin periodane; acetic acid; triethylamine; 2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; palladium on activated charcoal; L-(+)-diisopropyl tartrate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)70631-9

upstream raw materials:

Toluene-4-sulfonic acid (E)-(2S,6R)-2-[(2S,3S,4S,6R)-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-6-methyl-heptyl]-6-[(2R,4S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4-methyl-nona-4,8-dienyl ester

benzyl bromide

3-(p-methoxybenzyloxy)propanal

(S)-2-[(2R,3S)-3-((R)-3-Benzyloxy-2-methyl-propyl)-oxiranyl]-2-methoxy-ethanol

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