184774-09-2

Basic information

• Product Name: N,N-Dibenzyl-L-phenylalanine methyl ester
• Synonyms: N-Dibenzyl-L-phenylalanine Methyl ester;N,N-Dibenzyl-L-phenylalanine methyl ester;methyl (2S)-2-(dibenzylamino)-3-phenylpropanoate
• CAS NO: 184774-09-2
• Molecular Formula: C₂₄H₂₅NO₂
• Molecular Weight: 359.4608
• Mol File: 184774-09-2.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N,N-Dibenzyl-L-phenylalanine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dibenzyl-L-phenylalanine methyl ester(184774-09-2)
• EPA Substance Registry System: N,N-Dibenzyl-L-phenylalanine methyl ester(184774-09-2)

Safety Data

• Hazardous Substances Data: 184774-09-2(Hazardous Substances Data)

Upstream product

• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 100-39-0 benzyl bromide 
• 63-91-2 L-phenylalanine 
• 100-52-7 benzaldehyde 
• 27000-00-6 methyl 2-hydroxy-3-phenylpropionate 
• 103-49-1 dibenzylamine 
• 828-01-3 D-phenyllactic acid 

Downstream Products

• 103-25-3 3-phenylpropanoic acid methyl ester 
• 131150-39-5 (S)-2-(dibenzylamino)-1-phenylpentan-3-one 
• 1239425-57-0 BnO-Lac-Val-N-Me-Gln(Trt)-Ahppa-OtBu 
• 1239425-59-2 N-Cbz-N-Me-Gln(Trt)-Ahppa-OtBu 
• 951637-18-6 (3S,4S)-tert-butyl 4-amino-3-hydroxy-5-phenylpentanoate 
• 188774-99-4 tert-butyl 4-(N,N-dibenzylamino)-3-oxo-5-phenylpentanoate 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 111060-52-7 (S)-2-(dibenzylamino)-3-phenylpropan-1-ol 

Relevant articles and documents

Design, synthesis and evaluation of the antibacterial activity of new Linezolid dipeptide-type analogues

Worldwide studies towards development of new drugs with a lower rate in emergence of bacterial resistance have been conducted. The molecular docking analysis gives a possibility to predict the activity of new compounds before to perform their synthesis. In this work, the molecular docking analysis of 64 Linezolid dipeptide-type analogues was performed to predict their activity. The most negative scores correspond to six Fmoc-protected analogues (9as, 9bs, 9bu, 10as, 10ax and 10ay) where Fmoc group interacts in PTC for Linezolid. Twenty-six different Fmoc-protected Linezolid dipeptide-type analogues 9(as-bz) and 10(as-bz) were synthesized and tested in antimicrobial experiments. Compounds 9as, 9ay, 9ax, 10as, 10ay and 9bu show significant activity against group A Streptococcus clinical isolated. Analogue 10ay also display high activity against ATCC 25923 Staphylococcus aureus strain and MRSA-3, MRSA-4 and MRSA-5 clinical isolates, with MIC values lower than Linezolid. The highest activity against multidrug-resistant clinical isolates of Mycobacterium tuberculosis was exhibited by 9bu. Finally, a cytotoxicity assay with ARPE-19 human cells revealed a non-cytotoxic effect of 9bu and 10ay at 50 and 25 μM, respectively.

N-benzyl-protection of amino acid derivatives by reductive alkylation with α-picoline-borane

A convenient method for N-protection of amino acid derivatives with a benzyl group by reductive alkylation of amino acid derivatives with α-picoline-borane is described. Amino acid esters or amino alcohols were treated with aryl aldehydes in methanol/acetic acid in the presence of -picoline-borane to give N-benzyl-protected amino acid derivatives in good yields. Georg Thieme Verlag Stuttgart - New York.

Boron-mediated aldol reactions of ethyl α-(N,N)-dibenzylamino ketones: Control of enolisation geometry and aldehyde π-facial selectivity

The boron-mediated aldol reactions of a range of chiral α-(N,N)-dibenzylamino ketones with aldehydes can be controlled to provide stereodefined adducts. Complementary induction can be achieved with cHex2BCl/Me2NEt leading to preferential formation of the 1,2-anti-2,4-syn adducts, while Bu2BOTfiPr2NEt provides 1,2-syn-2,4-anti adducts.