(3S,6S)-3-(1-methylethyl)-6-(phenylmethyl)piperazine-2,5-dione

Base Information

• Chemical Name: (3S,6S)-3-(1-methylethyl)-6-(phenylmethyl)piperazine-2,5-dione
• CAS No.: 35590-86-4
• Molecular Formula: C₁₄H₁₈N₂O₂
• Molecular Weight: 246.309
• Mol file: 35590-86-4.mol

Synonyms:(3S,6S)-3-(1-methylethyl)-6-(phenylmethyl)piperazine-2,5-dione

Chemical Property of (3S,6S)-3-(1-methylethyl)-6-(phenylmethyl)piperazine-2,5-dione

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Cyclo(L-Phe-L-Val) ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Cyclo(L-Phe-L-Val) is a metabolite of the sponge bacterium Pseudoalteromonas sp. NJ6-3-1 that can autoinduce production of antibacterial substances active against S. aureus when co-cultured at a low cell density. It induces neurite outgrowth and branching of chick cortical neurons in vitro when used at concentrations of 16 and 32 μM. It increases phosphorylation of the PI3K substrate Akt, and neurite outgrowth induced by cyclo(L-Phe-L-Val) can be blocked by the PI3K inhibitor LY294002 . Cyclo(L-Phe-L-Val) enhances axon sprouting of calcitonin gene-related protein positive (CGRP+) primary afferents in the spinal cord following crush injury and of serotonin neurons in uninjured spinal cord. Cyclo(L-Phe-L-Val) is also a bitter taste component of cocoa and roasted coffee.

Technology Process of (3S,6S)-3-(1-methylethyl)-6-(phenylmethyl)piperazine-2,5-dione

There total 21 articles about (3S,6S)-3-(1-methylethyl)-6-(phenylmethyl)piperazine-2,5-dione 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: 99.0%

tert-butyl (S)-2-[(S)-2-tert-butoxycarbonylamino-3-methylbutyrylamino]-3-phenylpropionate (1202014-16-1) → (3S,6S)-3-(1-methylethyl)-6-(phenylmethyl)piperazine-2,5-dione (35590-86-4)

Guidance literature:

In water; at 250 ℃; for 0.166667h; under 7757.43 Torr; Microwave irradiation;

DOI:10.3390/molecules14082836

Reference yield: 98.0%

ethyl N'-(tert-butoxycarbonyl)-L-phenylalanyl-L-valinate (93510-10-2) → (3S,6S)-3-(1-methylethyl)-6-(phenylmethyl)piperazine-2,5-dione (35590-86-4)

Guidance literature:

for 0.133333h; microwave irradiation;

DOI:10.1055/s-2005-918473

Reference yield: 90.0%

L-phenylalanyl-L-valine (3918-90-9) → (3S,6S)-3-(1-methylethyl)-6-(phenylmethyl)piperazine-2,5-dione (35590-86-4)

Guidance literature:

In water; at 180 ℃; for 0.166667h; Microwave irradiation; Sealed tube;

DOI:10.1055/s-0037-1612376

upstream raw materials:

(3S,6S)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-6-benzyl-piperazine-2,5-dione

L-valyl-L-phenylalanine methyl ester

ethyl N'-(tert-butoxycarbonyl)-L-phenylalanyl-L-valinate

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

L-phenylalanine hydrochloride

(2S,5S)-di-tert-butyl 2-benzyl-5-isopropyl-3,6-dioxopiperazine-1,4-dicarboxylate

L-Valine methyl ester

methyl (2S)-2-amino-3-phenylpropanoate

Refernces

• 1、 De Zorzi, Rita,Deganutti, Caterina,Garcia, Ana M.,Kralj, Slavko,Kurbasic, Marina,Marchesan, Silvia,Parisi, Evelina,Semeraro, Sabrina. "Microwave-Assisted Cyclization of Unprotected Dipeptides in Water to 2,5-Piperazinediones and Self-Assembly Study of Products and Reagents". . p. 2839 - 2844. Retrieved 2019/07/05.
• 2、 Laville, Rmi,Nguyen, Thanh Binh,Moriou, Cline,Petek, Sylvain,Debitus, Ccile,Al-Mourabit, Ali. "Marine natural occurring 2,5-diketopiperazines: Isolation, synthesis and optical properties". . p. 1351 - 1366. Retrieved 2015/03/04.