ethyl 3-[3-(tert-butyldimethylsiloxy)propyl]-6-(tert-butyldiphenylsiloxy)hex-2-enoate

Base Information

• Chemical Name: ethyl 3-[3-(tert-butyldimethylsiloxy)propyl]-6-(tert-butyldiphenylsiloxy)hex-2-enoate
• CAS No.: 503000-29-1
• Molecular Formula: C₃₃H₅₂O₄Si₂
• Molecular Weight: 568.944

Synonyms:ethyl 3-[3-(tert-butyldimethylsiloxy)propyl]-6-(tert-butyldiphenylsiloxy)hex-2-enoate

Chemical Property of ethyl 3-[3-(tert-butyldimethylsiloxy)propyl]-6-(tert-butyldiphenylsiloxy)hex-2-enoate

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Technology Process of ethyl 3-[3-(tert-butyldimethylsiloxy)propyl]-6-(tert-butyldiphenylsiloxy)hex-2-enoate

There total 2 articles about ethyl 3-[3-(tert-butyldimethylsiloxy)propyl]-6-(tert-butyldiphenylsiloxy)hex-2-enoate 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: 96.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 1-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-heptan-4-one (503000-45-1) → ethyl 3-[3-(tert-butyldimethylsiloxy)propyl]-6-(tert-butyldiphenylsiloxy)hex-2-enoate (503000-29-1)

Guidance literature:

With sodium hydride; In 1,2-dimethoxyethane; for 6h; Heating;

DOI:10.1021/ol034020s

Reference yield:

4-(tert-butyldiphenylsilyloxy)-N-methoxy-N-methylbutanamide (215251-69-7) → ethyl 3-[3-(tert-butyldimethylsiloxy)propyl]-6-(tert-butyldiphenylsiloxy)hex-2-enoate (503000-29-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / t-BuLi / tetrahydrofuran; pentane / -78 - 20 °C

2: 96 percent / NaH / 1,2-dimethoxy-ethane; various solvent(s) / 6 h / Heating

With tert.-butyl lithium; sodium hydride; In tetrahydrofuran; 1,2-dimethoxyethane; pentane; 2: Horner-Emmons reaction;

DOI:10.1021/ol034020s

Reference yield: 99.0%

ethyl 3-[3-(tert-butyldimethylsiloxy)propyl]-6-(tert-butyldiphenylsiloxy)hex-2-enoate (503000-29-1) → 3-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-6-(tert-butyl-diphenyl-silanyloxy)-hex-2-en-1-ol (503000-46-2)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

DOI:10.1021/ol034020s

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

1-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-heptan-4-one

4-(tert-butyldiphenylsilyloxy)-N-methoxy-N-methylbutanamide

Downstream raw materials:

3-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-6-(tert-butyl-diphenyl-silanyloxy)-hex-2-en-1-ol

3-((S)-4-Oxo-1-vinyl-cyclohex-2-enyl)-propionic acid

(4S)-4-(2-carbamoylethyl)-4-vinyl-2-cyclohexene-1-one

(1S,4R)-4-(3-Hydroxy-propyl)-4-vinyl-cyclohex-2-enol

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