(2S,5S)-tert-butyl 5-(benzyloxymethyl)-2-[(S)-1-(tert-butyldiphenylsilyloxy)oct-7-en-4-yl]-2-vinylpyrrolidine-1-carboxylate

Base Information

Chemical Name:(2S,5S)-tert-butyl 5-(benzyloxymethyl)-2-[(S)-1-(tert-butyldiphenylsilyloxy)oct-7-en-4-yl]-2-vinylpyrrolidine-1-carboxylate
CAS No.:879572-72-2
Molecular Formula:C₄₃H₅₉NO₄Si
Molecular Weight:682.031
Hs Code.:

Synonyms:(2S,5S)-tert-butyl 5-(benzyloxymethyl)-2-[(S)-1-(tert-butyldiphenylsilyloxy)oct-7-en-4-yl]-2-vinylpyrrolidine-1-carboxylate

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Chemical Property of (2S,5S)-tert-butyl 5-(benzyloxymethyl)-2-[(S)-1-(tert-butyldiphenylsilyloxy)oct-7-en-4-yl]-2-vinylpyrrolidine-1-carboxylate

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Technology Process of (2S,5S)-tert-butyl 5-(benzyloxymethyl)-2-[(S)-1-(tert-butyldiphenylsilyloxy)oct-7-en-4-yl]-2-vinylpyrrolidine-1-carboxylate

There total 1 articles about (2S,5S)-tert-butyl 5-(benzyloxymethyl)-2-[(S)-1-(tert-butyldiphenylsilyloxy)oct-7-en-4-yl]-2-vinylpyrrolidine-1-carboxylate 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:

: 5-benzyloxymethyl-2-{1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-pent-4-enyl}-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 2065-66-9
methyl-triphenylphosphonium iodide

: 879572-72-2
(2S,5S)-tert-butyl 5-(benzyloxymethyl)-2-[(S)-1-(tert-butyldiphenylsilyloxy)oct-7-en-4-yl]-2-vinylpyrrolidine-1-carboxylate

Guidance literature:: methyl-triphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 - 20 ℃;

5-benzyloxymethyl-2-{1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-pent-4-enyl}-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester; In tetrahydrofuran; hexane; for 1h;
DOI:10.1021/ol053010j

Reference yield: 98.0%

: 879572-72-2
(2S,5S)-tert-butyl 5-(benzyloxymethyl)-2-[(S)-1-(tert-butyldiphenylsilyloxy)oct-7-en-4-yl]-2-vinylpyrrolidine-1-carboxylate

: 879572-75-5
(2S,5R,10S)-tert-butyl 5-(benzyloxymethyl)-10-[3'-(tert-butyldiphenylsilanyloxy)propyl]-1-azaspiro[4,5]dec-6-ene-1-carboxylate

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 40 ℃; for 1h;
DOI:10.1021/ol053010j

Reference yield:

: 879572-72-2
(2S,5S)-tert-butyl 5-(benzyloxymethyl)-2-[(S)-1-(tert-butyldiphenylsilyloxy)oct-7-en-4-yl]-2-vinylpyrrolidine-1-carboxylate

: 879572-78-8
(2S,5S,6S)-tert-butyl 2-(benzyloxymethyl)-6-(3'-oxo-propyl)-1-azaspiro[4,5]decane-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / second generation Grubbs' catalyst / CH₂Cl₂ / 1 h / 40 °C

2: 95 percent / hydrogen; triethylamine / Pd/C / methanol / 12 h / 20 °C

3: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 20 °C

4: 96 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ol053010j