(E)-benzyl 5-(methoxycarbonyloxy)-1-phenylpent-3-enyl(tosylcarbamoyl)carbamate

Base Information

Chemical Name:(E)-benzyl 5-(methoxycarbonyloxy)-1-phenylpent-3-enyl(tosylcarbamoyl)carbamate
CAS No.:1245904-34-0
Molecular Formula:C₂₉H₃₀N₂O₈S
Molecular Weight:566.632
Hs Code.:

Synonyms:(E)-benzyl 5-(methoxycarbonyloxy)-1-phenylpent-3-enyl(tosylcarbamoyl)carbamate

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Chemical Property of (E)-benzyl 5-(methoxycarbonyloxy)-1-phenylpent-3-enyl(tosylcarbamoyl)carbamate

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Technology Process of (E)-benzyl 5-(methoxycarbonyloxy)-1-phenylpent-3-enyl(tosylcarbamoyl)carbamate

There total 5 articles about (E)-benzyl 5-(methoxycarbonyloxy)-1-phenylpent-3-enyl(tosylcarbamoyl)carbamate 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: 53.0%

: 1245904-33-9
(E)-benzyl 5-(methoxycarbonyloxy)-1-phenylpent-3-enylcarbamate

: 4083-64-1
Tosyl isocyanate

: 1245904-34-0
(E)-benzyl 5-(methoxycarbonyloxy)-1-phenylpent-3-enyl(tosylcarbamoyl)carbamate

Guidance literature:: (E)-benzyl 5-(methoxycarbonyloxy)-1-phenylpent-3-enylcarbamate; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 0.25h;

Tosyl isocyanate; In diethyl ether; hexane; at -78 ℃; for 1.08333h;
DOI:10.1021/ol101755m

Reference yield:

: 100-52-7
benzaldehyde

: 1245904-34-0
(E)-benzyl 5-(methoxycarbonyloxy)-1-phenylpent-3-enyl(tosylcarbamoyl)carbamate

Guidance literature:: Multi-step reaction with 3 steps

1: 1,1,1,3,3,3-hexamethyl-disilazane; iodine / acetonitrile / Inert atmosphere; Schlenk technique

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 80 °C / Inert atmosphere; Schlenk technique

3: n-butyllithium / diethyl ether / -78 °C / Inert atmosphere; Schlenk technique

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; n-butyllithium; iodine; 1,1,1,3,3,3-hexamethyl-disilazane; In diethyl ether; toluene; acetonitrile;
DOI:10.3762/bjoc.12.107

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 1245904-34-0
(E)-benzyl 5-(methoxycarbonyloxy)-1-phenylpent-3-enyl(tosylcarbamoyl)carbamate

Guidance literature:: Multi-step reaction with 3 steps

1: 1,1,1,3,3,3-hexamethyl-disilazane; iron(II) sulfate / acetonitrile / Inert atmosphere; Schlenk technique

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 80 °C / Inert atmosphere; Schlenk technique

3: n-butyllithium / diethyl ether / -78 °C / Inert atmosphere; Schlenk technique

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; n-butyllithium; iron(II) sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; In diethyl ether; toluene; acetonitrile;
DOI:10.3762/bjoc.12.107