(+)-methyl (S(S),3S)-N-(p-toluenesulfinyl)-3-amino-5-(2-methyl-1,3-dioxolan-2-yl)pentanoate

Base Information

Chemical Name:(+)-methyl (S(S),3S)-N-(p-toluenesulfinyl)-3-amino-5-(2-methyl-1,3-dioxolan-2-yl)pentanoate
CAS No.:1243634-44-7
Molecular Formula:C₁₇H₂₅NO₅S
Molecular Weight:355.455
Hs Code.:

Synonyms:(+)-methyl (S(S),3S)-N-(p-toluenesulfinyl)-3-amino-5-(2-methyl-1,3-dioxolan-2-yl)pentanoate

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Chemical Property of (+)-methyl (S(S),3S)-N-(p-toluenesulfinyl)-3-amino-5-(2-methyl-1,3-dioxolan-2-yl)pentanoate

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Technology Process of (+)-methyl (S(S),3S)-N-(p-toluenesulfinyl)-3-amino-5-(2-methyl-1,3-dioxolan-2-yl)pentanoate

There total 4 articles about (+)-methyl (S(S),3S)-N-(p-toluenesulfinyl)-3-amino-5-(2-methyl-1,3-dioxolan-2-yl)pentanoate 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: 75.0%

: 79-20-9
acetic acid methyl ester

: 1355076-15-1
(S(S))-(+)-3-(2-methyl-1,3-dioxolan-2-yl)propylidene-p-toluenesulfinamide

: 1243634-44-7
(+)-methyl (S(S),3S)-N-(p-toluenesulfinyl)-3-amino-5-(2-methyl-1,3-dioxolan-2-yl)pentanoate

Guidance literature:: acetic acid methyl ester; With sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; at -78 ℃; Inert atmosphere;

(S(S))-(+)-3-(2-methyl-1,3-dioxolan-2-yl)propylidene-p-toluenesulfinamide; In tetrahydrofuran; diethyl ether; at -78 ℃; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; diethyl ether; optical yield given as %de; Inert atmosphere;
DOI:10.1021/ol1017118

Reference yield:

: 79-20-9
acetic acid methyl ester

: 1355076-15-1
(S(S))-(+)-3-(2-methyl-1,3-dioxolan-2-yl)propylidene-p-toluenesulfinamide

: 1243634-44-7
(+)-methyl (S(S),3S)-N-(p-toluenesulfinyl)-3-amino-5-(2-methyl-1,3-dioxolan-2-yl)pentanoate

: 1138339-14-6
(SS,S)-(+)-methyl-N-(p-toluenesulfinyl)-5-amino-7-(2-methyl-1,3-dioxolan-2-yl)-3-oxoheptanoate

Guidance literature:: acetic acid methyl ester; With sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; at -78 ℃; Inert atmosphere;

(S(S))-(+)-3-(2-methyl-1,3-dioxolan-2-yl)propylidene-p-toluenesulfinamide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 3h; Inert atmosphere;
DOI:10.1021/ol9002948

Reference yield:

: 24108-29-0
3-(2-methyl-[1,3]dioxolan-2-yl)-propionaldehyde

: 1243634-44-7
(+)-methyl (S(S),3S)-N-(p-toluenesulfinyl)-3-amino-5-(2-methyl-1,3-dioxolan-2-yl)pentanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: titanium(IV) tetraethanolate / dichloromethane / 20 °C / Inert atmosphere

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

2.2: 2 h / -78 °C / Inert atmosphere

With titanium(IV) tetraethanolate; sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo202652f