methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-3-hydroxy-7-phenyl-hept-6-ynoate

Base Information

Chemical Name:methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-3-hydroxy-7-phenyl-hept-6-ynoate
CAS No.:626249-41-0
Molecular Formula:C₂₅H₄₀O₄Si
Molecular Weight:432.676
Hs Code.:

Synonyms:methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-3-hydroxy-7-phenyl-hept-6-ynoate

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Chemical Property of methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-3-hydroxy-7-phenyl-hept-6-ynoate

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Technology Process of methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-3-hydroxy-7-phenyl-hept-6-ynoate

There total 4 articles about methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-3-hydroxy-7-phenyl-hept-6-ynoate 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: 66.0%

: 130602-09-4
6-phenylhex-5-yn-1-al

: 161232-10-6
6-(tert-butyl-dimethylsilanoxy)hexanoic acid methyl ester

: 626249-41-0
methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-3-hydroxy-7-phenyl-hept-6-ynoate

Guidance literature:: 6-(tert-butyl-dimethylsilanoxy)hexanoic acid methyl ester; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.583333h;

6-phenylhex-5-yn-1-al; In tetrahydrofuran; at -78 ℃; for 3h;
DOI:10.1021/ja037423w

Reference yield:

: 928-90-5
5-hexyl-1-ol

: 626249-41-0
methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-3-hydroxy-7-phenyl-hept-6-ynoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 98 percent / CuI; iPr₂NH; Pd(Ph₃)4 / tetrahydrofuran / 20 °C

2.1: 95 percent / PCC / CH₂Cl₂ / 5 h / 35 °C

3.1: iPr₂NH; n-BuLi / hexane; tetrahydrofuran / 0.58 h / -78 °C

3.2: 66 percent / tetrahydrofuran / 3 h / -78 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ja037423w

Reference yield:

: 69936-53-4
6-phenylhex-5-yn-1-ol

: 626249-41-0
methyl 2-[4-(tert-butyldimethylsilanyloxy)butyl]-3-hydroxy-7-phenyl-hept-6-ynoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 95 percent / PCC / CH₂Cl₂ / 5 h / 35 °C

2.1: iPr₂NH; n-BuLi / hexane; tetrahydrofuran / 0.58 h / -78 °C

2.2: 66 percent / tetrahydrofuran / 3 h / -78 °C

With n-butyllithium; diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ja037423w