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

Base Information

• Chemical Name: (2R)-methyl N-[2-phenyl-2-[tetrahydropyran-(2RS)-2-yloxy]acetyl]-L-alaninate
• CAS No.: 199870-96-7
• Molecular Formula: C₁₇H₂₃NO₅
• Molecular Weight: 321.373
• Mol file: 199870-96-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (2R)-methyl N-[2-phenyl-2-[tetrahydropyran-(2RS)-2-yloxy]acetyl]-L-alaninate 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%

L-Alanine methyl ester (10065-72-2) + (1R)-S-ethyl [1-phenyl-1-tetrahydropyran-(2RS)-2-yloxy]-thioacetate (157982-28-0) → (2R)-methyl N-[2-phenyl-2-[tetrahydropyran-(2RS)-2-yloxy]acetyl]-L-alaninate (199870-96-7)

Guidance literature:

With silver trifluoroacetate; In acetonitrile; at 50 ℃; for 16h;

DOI:10.1016/S0040-4020(97)01010-7

Reference yield:

benzaldehyde (100-52-7) → (2R)-methyl N-[2-phenyl-2-[tetrahydropyran-(2RS)-2-yloxy]acetyl]-L-alaninate (199870-96-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / NaHMDS, pyridine / tetrahydrofuran

2: 94 percent / TsOH / CH₂Cl₂

3: 1.) trifluoroacetic anhydride, pyridine, 2.) aq. LiOH / 1.) CH₂Cl₂, 0 deg C, 15 min, 2.) THF, from 0 deg C to RT

4: AgOCOCF₃ / acetonitrile

With pyridine; lithium hydroxide; sodium hexamethyldisilazane; silver trifluoroacetate; toluene-4-sulfonic acid; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1039/c39940001653

Reference yield:

(1R,3R)-1,3-dithiane-1,3-dioxide-2-[(1R)-1-phenyl]methanol (158060-53-8) → (2R)-methyl N-[2-phenyl-2-[tetrahydropyran-(2RS)-2-yloxy]acetyl]-L-alaninate (199870-96-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / TsOH / CH₂Cl₂

2: 1.) trifluoroacetic anhydride, pyridine, 2.) aq. LiOH / 1.) CH₂Cl₂, 0 deg C, 15 min, 2.) THF, from 0 deg C to RT

3: AgOCOCF₃ / acetonitrile

With pyridine; lithium hydroxide; silver trifluoroacetate; toluene-4-sulfonic acid; trifluoroacetic anhydride; In dichloromethane; acetonitrile;

DOI:10.1039/c39940001653

upstream raw materials:

L-Alanine methyl ester

(1R)-S-ethyl [1-phenyl-1-tetrahydropyran-(2RS)-2-yloxy]-thioacetate

benzaldehyde

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

Downstream raw materials:

(2R)-methyl N-[(2-hydroxy-2-phenyl)acetyl]-L-alaninate

(S)-2-(2-Hydroxy-2-phenyl-acetylamino)-propionic acid methyl ester