D-Aspartic acid, 3-methyl-N-[(4-methylphenyl)sulfonyl]-, dimethyl ester, (3S)-

Base Information

• Chemical Name: D-Aspartic acid, 3-methyl-N-[(4-methylphenyl)sulfonyl]-, dimethyl ester, (3S)-
• CAS No.: 616866-46-7
• Molecular Formula: C14H19NO6S
• Molecular Weight: 329.374
• Mol file: 616866-46-7.mol

Synonyms:

Chemical Property of D-Aspartic acid, 3-methyl-N-[(4-methylphenyl)sulfonyl]-, dimethyl ester, (3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-Aspartic acid, 3-methyl-N-[(4-methylphenyl)sulfonyl]-, dimethyl ester, (3S)-

There total 2 articles about D-Aspartic acid, 3-methyl-N-[(4-methylphenyl)sulfonyl]-, dimethyl ester, (3S)- 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: 89.0%

(2R)-N-(p-toluenesulfonyl)-aspartic acid dimethyl ester (616866-44-5) + methyl iodide (74-88-4) → (2R,3S)-N-(p-toluenesulfonyl)-3-methylaspartic acid dimethyl ester (616866-46-7)

Guidance literature:

(2R)-N-(p-toluenesulfonyl)-aspartic acid dimethyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2h;

methyl iodide; In tetrahydrofuran; for 15h;

DOI:10.1021/ol035156t

Reference yield:

dimethyl D-aspartate (6384-18-5,40149-67-5,88067-96-3) → (2R,3S)-N-(p-toluenesulfonyl)-3-methylaspartic acid dimethyl ester (616866-46-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 79 percent / Et₃N / tetrahydrofuran / 16 h / 20 °C

2.1: LiHMDS / tetrahydrofuran / 2 h / -78 °C

2.2: 89 percent / tetrahydrofuran / 15 h / 20 °C

With triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1021/jo048455k

Reference yield: 98.0%

(2R,3S)-N-(p-toluenesulfonyl)-3-methylaspartic acid dimethyl ester (616866-46-7) → (1R,2S)-N-(3-hydroxy-1-hydroxymethyl-2-methyl-propyl)-4-methylbenzenesulfonamide (616866-48-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1021/ol035156t

upstream raw materials:

(2R)-N-(p-toluenesulfonyl)-aspartic acid dimethyl ester

methyl iodide

dimethyl D-aspartate

Downstream raw materials:

(1R,2S)-N-(3-hydroxy-1-hydroxymethyl-2-methyl-propyl)-4-methylbenzenesulfonamide

nupharolutine

(–)-castoramine

deoxynupharidine

Refernces

• 1、 Moran, Wesley J.,Goodenough, Katharine M.,Raubo, Piotr,Harrity, Joseph P. A.. "A Concise Asymmetric Route to Nuphar Alkaloids. A Formal Synthesis of (-)-Deoxynupharidine". . p. 3427 - 3429. Retrieved 2007/10/03.