TMC-58B

Base Information

• Chemical Name: TMC-58B
• CAS No.: 58115-31-4
• Molecular Formula: C25H26N2O3
• Molecular Weight: 402.493
• Mol file: 58115-31-4.mol

Synonyms:

Chemical Property of TMC-58B

Chemical Property:

• Vapor Pressure: 5.61E-22mmHg at 25°C
• Boiling Point: 723.6°Cat760mmHg
• PKA: 13.31±0.46(Predicted)
• Flash Point: 391.4°C
• PSA: 78.43000
• Density: 1.191g/cm³
• LogP: 3.52930

Purity/Quality:

98%min ^*data from raw suppliers

Aurantiamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: One of two new amide-type alkaloids recently isolated from the seeds of Piper aurantiacurn, the structure of this base has been elucidated from chemical degradation and spectroscopic investigations and confirmed by synthesis, the latter also establishing the absolute configuration.

Technology Process of TMC-58B

There total 19 articles about TMC-58B 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: 82.0%

aurantiamide acetate (80780-41-2,112924-28-4,125276-43-9,138812-57-4,139893-26-8,56121-42-7) → N-(N-benzoyl-L-phenylalanyl)-L-phenylalaninol (58115-31-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h; Reflux;

Reference yield: 79.0%

N-benzoyl-L-phenylalanine (2566-22-5) + L-Phenylalaninol (3182-95-4) → N-(N-benzoyl-L-phenylalanyl)-L-phenylalaninol (58115-31-4)

Guidance literature:

With 4-methyl-morpholine; isobutyl chloroformate; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1002/cjoc.201600468

Reference yield: 8.0%

(R)-2-amino-3-phenylpropanol (5267-64-1) + N-benzoyl-D-phenylalanine (37002-52-1) → N-(N-benzoyl-L-phenylalanyl)-L-phenylalaninol (58115-31-4) + dia-aurantiamide (150881-04-2)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; 1.) 0 deg C, 4 h; 2.) room temperature, 2 h;

DOI:10.1016/0031-9422(81)80116-1

upstream raw materials:

(R)-2-amino-3-phenylpropanol

N-benzoyl-D-phenylalanine

aurantiamide acetate

benzoyl chloride

Downstream raw materials:

DL-N-benzoylphenylalanine

aurantiamide acetate

Refernces

• 1、 Nanjo, Takeshi,Kato, Natsuki,Zhang, Xuan,Takemoto, Yoshiji. "A Hydroperoxide-Mediated Decarboxylation of α-Ketoacids Enables the Chemoselective Acylation of Amines". supporting information. p. 15504 - 15507. Retrieved 2019/11/14.
• 2、 -. "PHENYLALANINE DIPEPTIDE DERIVATIVES, COMPOSITIONS AND USE THEREOF". Page/Page column 15. . Retrieved 2009/10/06.