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

Base Information

• Chemical Name: (Ss,5S,2E)-(+)-methyl N-(tert-butylsulfinyl)-5-amino-7-(2-phenyl-1,3-dioxolan-2-yl)-hept-2-enoate
• CAS No.: 1355075-74-9
• Molecular Formula: C₂₁H₃₁NO₅S
• Molecular Weight: 409.547
• Mol file: 1355075-74-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (Ss,5S,2E)-(+)-methyl N-(tert-butylsulfinyl)-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: 90.0%

trimethyl phosphonoacetate (5927-18-4) + (Ss,3S)-(+)-N-(tert-butylsulfinyl)-3-amino-5-(2-phenyl-1,3-dioxolan-2-yl)pentanal (1355075-66-9) → (Ss,5S,2E)-(+)-methyl N-(tert-butylsulfinyl)-5-amino-7-(2-phenyl-1,3-dioxolan-2-yl)-hept-2-enoate (1355075-74-9)

Guidance literature:

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

(Ss,3S)-(+)-N-(tert-butylsulfinyl)-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: 90.0%

→ (Ss,5S,2E)-(+)-methyl N-(tert-butylsulfinyl)-5-amino-7-(2-phenyl-1,3-dioxolan-2-yl)-hept-2-enoate (1355075-74-9)

Guidance literature:

Reference yield:

(S)-(+)-3-(2-phenyl-1,3-dioxalan-2-yl)propylidene-tert-butylsulfinamide (1355075-50-1) → (Ss,5S,2E)-(+)-methyl N-(tert-butylsulfinyl)-5-amino-7-(2-phenyl-1,3-dioxolan-2-yl)-hept-2-enoate (1355075-74-9)

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 / 0.17 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

upstream raw materials:

acrylic acid methyl ester

(S)-(+)-3-(2-phenyl-1,3-dioxalan-2-yl)propylidene-tert-butylsulfinamide

(Ss,3S)-(+)-methyl N-(tert-butylsulfinyl)-3-amino-5-(2-phenyl-1,3-dioxolan-2-yl)pentanoate

trimethyl phosphonoacetate

Downstream raw materials:

(5S,2E)-(+)-methyl (3,4-dihydro-5-phenyl-2H-pyrrol-2-yl)-but-2-enoate

C₁₅H₁₇NO₃

(E)-(S)-(+)-methyl 4-(5-oxo-1-phenylpyrrolidin-2-yl)-but-2-enoate

(1S,2R,3R,6S)-(-)-methyl 3-phenyl-7-aza-8-oxatricyclo[4.2.1.0(3,7)]nonane-2-carboxylate