L-Alanine, N-(hydroxyphenylacetyl)-, methyl ester, (S)-

Base Information

• Chemical Name: L-Alanine, N-(hydroxyphenylacetyl)-, methyl ester, (S)-
• CAS No.: 93200-02-3
• Molecular Formula: C12H15NO4
• Molecular Weight: 237.255
• Mol file: 93200-02-3.mol

Synonyms:

Chemical Property of L-Alanine, N-(hydroxyphenylacetyl)-, methyl ester, (S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Alanine, N-(hydroxyphenylacetyl)-, methyl ester, (S)-

There total 12 articles about L-Alanine, N-(hydroxyphenylacetyl)-, methyl ester, (S)- 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:

N-(phenylglyoxyl)-(S)-α-alanine methyl ester (79546-42-2) → (2R)-methyl N-[(2-hydroxy-2-phenyl)acetyl]-L-alaninate (79546-40-0) + N-((S)-mandelyl)-(S)-α-alanine methyl ester (93200-02-3)

Guidance literature:

With hydrogen; (+)-Cydiop-Rh^N; In tetrahydrofuran; at 25 ℃; for 20h; Product distribution; other catalysts;

DOI:10.1246/cl.1986.737

Reference yield:

L-Alanine methyl ester (10065-72-2) + (S)-Mandelic acid (17199-29-0) → N-((S)-mandelyl)-(S)-α-alanine methyl ester (93200-02-3)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jo501501z

Reference yield:

N-(phenylglyoxyl)-(S)-α-alanine methyl ester (79546-42-2) → (S)-2-(2-Hydroxy-2-phenyl-acetylamino)-propionic acid methyl ester (79546-40-0,93200-02-3)

Guidance literature:

With methanol; 1-naphthylphenylsilane; toluene-4-sulfonic acid; rhodium(I) complex of (+)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)-butane ((+)DIOP-Rh^N); Yield given. Multistep reaction; 1.) benzene, 20 deg C, 24 h; 40 deg C, 12 h, 2.) 40 deg C, 1h;

DOI:10.1246/cl.1981.823

upstream raw materials:

N-(phenylglyoxyl)-(S)-α-alanine methyl ester

(2R)-methyl N-[2-phenyl-2-[tetrahydropyran-(2RS)-2-yloxy]acetyl]-L-alaninate

benzaldehyde

(1R,3R)-1,3-dithiane-1,3-dioxide-2-[(1R)-1-phenyl]methanol

Downstream raw materials:

(S)-2-[2-Phenyl-2-(2,2,2-trifluoro-acetoxy)-acetylamino]-propionic acid methyl ester

Refernces

• 1、 Khalil, Zeinab G.,Huang, Xiao-Cong,Raju, Ritesh,Piggott, Andrew M.,Capon, Robert J.. "Shornephine A: Structure, chemical stability, and P-glycoprotein inhibitory properties of a rare diketomorpholine from an Australian marine-derived Aspergillus sp.". . p. 8700 - 8705. Retrieved 2014/12/12.
• 2、 Aggarwal, Varinder K.,Thomas, Abraham,Franklin, Richard J.. "trans-1,3-Dithiane-1,3-Dioxide, a New Chiral Acyl Anion Equivalent for the Preparation of Masked Activated Acids: Application to the Synthesis of α-Hydroxy Acid Derivatives". . p. 1653 - 1654. Retrieved 2007/10/02.