2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-3-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentan-1-one

Base Information

Chemical Name:2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-3-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentan-1-one
CAS No.:333968-40-4
Molecular Formula:C₃₈H₆₂O₅Si₂
Molecular Weight:655.078
Hs Code.:

Synonyms:2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-3-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentan-1-one

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Chemical Property of 2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-3-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentan-1-one

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Technology Process of 2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-3-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentan-1-one

There total 6 articles about 2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-3-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentan-1-one 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: 83.0%

: 333968-37-9
(R)-2-(tert-butyldimethylsilyloxy)-4-iodo-1-phenoxybutane

: 333968-39-1
(4R)-2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-2-cyclopenten-1-one

: 333968-40-4
2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-3-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentan-1-one

Guidance literature:: (R)-2-(tert-butyldimethylsilyloxy)-4-iodo-1-phenoxybutane; With tert.-butyl lithium; thien-2-yl(cyano)copper lithium; In tetrahydrofuran; diethyl ether; pentane; at -78 - -40 ℃;

(4R)-2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-2-cyclopenten-1-one; In tetrahydrofuran; diethyl ether; pentane; at -78 - -20 ℃; Further stages.;
DOI:10.1021/ol015613a

Reference yield:

: 108-95-2,27073-41-2
phenol

: 333968-40-4
2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-3-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentan-1-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 99 percent / tert-butyl methyl ester; molecular sieves 4 Angstroem / (S,S)-(salen)Co[OC(CF₃)3] / 16 h / -20 °C

2.1: imidazole / dimethylformamide / 48 h / 20 °C

3.1: 3.21 g / NaI / acetone / Heating

4.1: tert-BuLi; (2-thienyl)Cu(CN)Li / pentane; diethyl ether; tetrahydrofuran / -78 - -40 °C

4.2: 83 percent / diethyl ether; tetrahydrofuran; pentane / -78 - -20 °C

With 1H-imidazole; tert-butyl methyl ester; 4 A molecular sieve; tert.-butyl lithium; thien-2-yl(cyano)copper lithium; sodium iodide; (S,S)-(salen)Co[OC(CF₃)3]; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetone; pentane;
DOI:10.1021/ol015613a

Reference yield:

: 70388-33-9
4-benzyloxybut-1-ene

: 333968-40-4
2-[4-(benzyloxy)butyl]-4-(tert-butyldimethylsilyloxy)-3-[3-(tert-butyldimethylsilyloxy)-4-phenoxybutyl]-cyclopentan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

1.2: 70 percent / K₃PO₄ / PdCl₂(dppf) / tetrahydrofuran; dimethylformamide; H₂O / 0.5 h / 20 °C

2.1: tert-BuLi; (2-thienyl)Cu(CN)Li / pentane; diethyl ether; tetrahydrofuran / -78 - -40 °C

2.2: 83 percent / diethyl ether; tetrahydrofuran; pentane / -78 - -20 °C

With 9-borabicyclo[3.3.1]nonane dimer; tert.-butyl lithium; thien-2-yl(cyano)copper lithium; In tetrahydrofuran; diethyl ether; pentane;
DOI:10.1021/ol015613a