benzoic acid 1-[2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-allyl ester

Base Information

• Chemical Name: benzoic acid 1-[2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-allyl ester
• CAS No.: 866007-66-1
• Molecular Formula: C₁₉H₂₈O₄Si
• Molecular Weight: 348.514

Synonyms:benzoic acid 1-[2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-allyl ester

Chemical Property of benzoic acid 1-[2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-allyl ester

Chemical Property:

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Technology Process of benzoic acid 1-[2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-allyl ester

There total 5 articles about benzoic acid 1-[2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-allyl ester 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: 98.0%

Benzoic acid 1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-allyl ester (866007-65-0) → benzoic acid 1-[2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-allyl ester (866007-66-1)

Guidance literature:

With periodic acid; In tetrahydrofuran; diethyl ether; at 20 ℃; for 12h;

DOI:10.1016/j.tetlet.2005.07.035

Reference yield:

(S)-5-(tert-Butyl-dimethyl-silanyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-1-en-3-ol (866007-64-9) → benzoic acid 1-[2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-allyl ester (866007-66-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 12 h / 20 °C

2: 98 percent / H₅IO₆ / tetrahydrofuran; diethyl ether / 12 h / 20 °C

With dmap; periodic acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/j.tetlet.2005.07.035

Reference yield:

tert-Butyl-[(S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propoxy]-dimethyl-silane (83685-85-2) → benzoic acid 1-[2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-allyl ester (866007-66-1)

Guidance literature:

Multi-step reaction with 4 steps

1: H₅IO₆ / tetrahydrofuran; diethyl ether / 0.25 h / 0 °C

2: tetrahydrofuran; diethyl ether / 0.03 h / 20 °C

3: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 12 h / 20 °C

4: 98 percent / H₅IO₆ / tetrahydrofuran; diethyl ether / 12 h / 20 °C

With dmap; periodic acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/j.tetlet.2005.07.035

upstream raw materials:

Benzoic acid 1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-allyl ester

(S)-5-(tert-Butyl-dimethyl-silanyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-1-en-3-ol

tert-Butyl-[(S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propoxy]-dimethyl-silane

(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionaldehyde

Downstream raw materials:

(S)-4-hydroxycyclopent-2-en-1-one

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