(2S-cis)-methyl ester 2-formyl-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid

Base Information

• Chemical Name: (2S-cis)-methyl ester 2-formyl-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid
• CAS No.: 192061-03-3
• Molecular Formula: C₁₄H₁₇NO₅
• Molecular Weight: 279.293
• Mol file: 192061-03-3.mol

Synonyms:(2S-cis)-methyl ester 2-formyl-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid

Chemical Property of (2S-cis)-methyl ester 2-formyl-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S-cis)-methyl ester 2-formyl-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid

There total 7 articles about (2S-cis)-methyl ester 2-formyl-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid 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: 92.0%

(2S-cis)-methyl ester 2-(hydroxymethyl)-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid (192061-02-2) → (2S-cis)-methyl ester 2-formyl-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid (192061-03-3)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(97)00865-4

Reference yield:

(2S-cis)-methyl ester 2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid (192061-01-1) → (2S-cis)-methyl ester 2-formyl-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid (192061-03-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / TBAF / tetrahydrofuran / 0.5 h

2: 92 percent / Dess-Martin reagent / CH₂Cl₂ / 2.5 h

With tetrabutyl ammonium fluoride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 1: Substitution / 2: Oxidation;

DOI:10.1016/S0040-4020(99)01046-7

Reference yield:

cis-3-[[(4-methoxyphenyl)methoxy]methyl]-oxiranemethanol → (2S-cis)-methyl ester 2-formyl-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid (192061-03-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 15.0 g

2: 86 percent / TBAF / tetrahydrofuran / 0.5 h

3: 92 percent / Dess-Martin reagent / CH₂Cl₂ / 2.5 h

With tetrabutyl ammonium fluoride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 2: Substitution / 3: Oxidation;

DOI:10.1016/S0040-4020(99)01046-7

upstream raw materials:

(2S-cis)-methyl ester 2-(hydroxymethyl)-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid

(2S-cis)-methyl ester 2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3-[(4-methoxyphenyl)methoxymethyl]-1-aziridinecarboxylic acid

4-methoxy-benzaldehyde

2-(4-methoxyphenyl)-4,7-dihydro-1,3-dioxepine

Downstream raw materials:

[2S-(2α,3α)]-methyl ester 2-[2-[2-amino-4-(methoxycarbonyl)-6-(methoxymethoxy)phenyl]-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-3-formyl-1-aziridinecarboxylic acid

[2S-(2α,3α)]-methyl ester 2-[1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-[(4-methoxycarbonyl)-2-(methoxymethoxy)-6-nitrophenyl]ethyl]-3-formyl-1-aziridinecarboxylic acid

[2S-(2α,3α)]-methyl ester 2-[1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-[(4-methoxycarbonyl)-2-(methoxymethoxy)-6-nitrophenyl]ethyl]-3-(hydroxymethyl)-1-aziridinecarboxylic acid

[2S-(2α,3α)]-methyl ester 2-[1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-[(4-methoxycarbonyl)-2-(methoxymethoxy)-6-nitrophenyl]ethyl]-3-[[(4-methoxyphenyl)methoxy]methyl]-1-aziridinecarboxylic acid