(Ss,5S,2E)-(+)-methyl N-(p-toluenesulfinyl)-5-amino-7-(2-phenyl-1,3-dioxolan-2-yl)-hept-2-enoate

Base Information

Chemical Name:(Ss,5S,2E)-(+)-methyl N-(p-toluenesulfinyl)-5-amino-7-(2-phenyl-1,3-dioxolan-2-yl)-hept-2-enoate
CAS No.:1360562-75-9
Molecular Formula:C₂₄H₂₉NO₅S
Molecular Weight:443.564
Hs Code.:

Synonyms:(Ss,5S,2E)-(+)-methyl N-(p-toluenesulfinyl)-5-amino-7-(2-phenyl-1,3-dioxolan-2-yl)-hept-2-enoate

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Chemical Property of (Ss,5S,2E)-(+)-methyl N-(p-toluenesulfinyl)-5-amino-7-(2-phenyl-1,3-dioxolan-2-yl)-hept-2-enoate

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Technology Process of (Ss,5S,2E)-(+)-methyl N-(p-toluenesulfinyl)-5-amino-7-(2-phenyl-1,3-dioxolan-2-yl)-hept-2-enoate

There total 4 articles about (Ss,5S,2E)-(+)-methyl N-(p-toluenesulfinyl)-5-amino-7-(2-phenyl-1,3-dioxolan-2-yl)-hept-2-enoate 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: 95.0%

: 5927-18-4
trimethyl phosphonoacetate

: 1360562-73-7
(Ss,3S)-(+)-N-(p-toluenesulfinyl)-3-amino-5-(2-phenyl-1,3-dioxolan-2-yl)pentanal

: 1360562-75-9
(Ss,5S,2E)-(+)-methyl N-(p-toluenesulfinyl)-5-amino-7-(2-phenyl-1,3-dioxolan-2-yl)-hept-2-enoate

Guidance literature:: trimethyl phosphonoacetate; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; Inert atmosphere;

(Ss,3S)-(+)-N-(p-toluenesulfinyl)-3-amino-5-(2-phenyl-1,3-dioxolan-2-yl)pentanal; In acetonitrile; at 20 ℃; optical yield given as %de; Inert atmosphere;
DOI:10.1021/jo202652f

Reference yield:

: (S)-(+)-3-(2-phenyl-1,3-dioxolan-2-yl)propylidene-p-toluenesulfinamide

: 1360562-75-9
(Ss,5S,2E)-(+)-methyl N-(p-toluenesulfinyl)-5-amino-7-(2-phenyl-1,3-dioxolan-2-yl)-hept-2-enoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran; diethyl ether / 1 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / toluene / 1 h / -78 °C

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

With sodium hexamethyldisilazane; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; diethyl ether; toluene; acetonitrile;
DOI:10.1021/jo202652f

Reference yield:

: 1360562-71-5
(Ss,3S)-(+)-methyl N-(p-toluenesulfinyl)-3-amino-5-(2-phenyl-1,3-dioxolan-2-yl)pentanoate

: 1360562-75-9
(Ss,5S,2E)-(+)-methyl N-(p-toluenesulfinyl)-5-amino-7-(2-phenyl-1,3-dioxolan-2-yl)-hept-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: diisobutylaluminium hydride / toluene / 1 h / -78 °C

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

With diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; acetonitrile;
DOI:10.1021/jo202652f