179915-11-8

Basic information

• Product Name: (R)-3-N-CBZ-AMINO-2,6-DIOXO-PIPERIDINE
• Synonyms: (R)-benzyl 2,6-dioxopiperidin-3-ylcarbamate;REF DUPL: R-3-N-Cbz-amino-2,6-Dioxo-piperidine;Carbamic acid, [(3R)-2,6-dioxo-3-piperidinyl]-, phenylmethyl ester (9CI);benzyl N-[(3R)-2,6-dioxopiperidin-3-yl]carbamate;(R)-3-Cbz-amino-2,6-dioxopiperidine
• CAS NO: 179915-11-8
• Molecular Formula: C13H14N2O4
• Molecular Weight: 262.26
• Mol File: 179915-11-8.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 520.2°Cat760mmHg
• Flash Point: 268.4°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 6.37E-11mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 10.58±0.20(Predicted)
• CAS DataBase Reference: (R)-3-N-CBZ-AMINO-2,6-DIOXO-PIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-N-CBZ-AMINO-2,6-DIOXO-PIPERIDINE(179915-11-8)
• EPA Substance Registry System: (R)-3-N-CBZ-AMINO-2,6-DIOXO-PIPERIDINE(179915-11-8)

Safety Data

• Hazardous Substances Data: 179915-11-8(Hazardous Substances Data)

Usage

General Description

(R)-3-N-CBZ-AMINO-2,6-DIOXO-PIPERIDINE is a chemical compound that is commonly used in pharmaceutical research and synthesis. It is a type of piperidine derivative that is often employed as a building block for the creation of various drugs and drug candidates. The compound has a carbobenzyloxy (CBZ) protecting group attached to the amino group, which can be selectively deprotected to reveal the free amine for further chemical reactions. The piperidine ring and the ketone groups make it a versatile molecule for the synthesis of diverse bioactive compounds. Additionally, it is known for its potential in the development of new medications for a variety of therapeutic purposes.

InChI:InChI=1/C13H14N2O4/c16-11-7-6-10(12(17)15-11)14-13(18)19-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,14,18)(H,15,16,17)/t10-/m1/s1

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 2650-64-8 Cbz-L-Gln 
• 13139-52-1 N-carbobenzoxy-D-glutamine 
• 56-85-9 L-glutamine 
• 501-53-1 benzyl chloroformate 
• 50516-14-8 Nα-benzyloxycarbonyl-glutamine 
• 13907-82-9 N²-benzyloxycarbonyl-L-glutamine methyl ester 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 67-56-1 methanol 
• 56-86-0 L-glutamic acid 

Downstream Products

• 202271-89-4 (R)-(+)-4-amino-2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3-dione 
• 202271-89-4 (S)-(-)-4-amino-2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3-dione 
• 1314881-81-6 padanamide B 
• 1426657-05-7 C₃₇H₆₀N₆O₉Si 
• 827026-45-9 3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione 
• 673485-72-8 (3R)-3-aminohexahydro-2,6-pyridinedione 
• 29883-25-8 (S)-3-aminopiperidine-2,6-dione 
• 73839-06-2 3-amino-3-methyl-piperidine-2,6-dione hydrochloride 
• 191732-76-0 2-(2,6-dioxo-3-piperidinyl)-5-amino-1H-isoindole-1,3(2H)-dione 
• 55003-81-1 2-(2,6-dioxo-3-piperidinyl)-5-nitro-1H-isoindole-1,3(2H)-dione 
• 90802-45-2 DL-3-amino-2,6-piperidinone hydrobromide 

Relevant articles and documents

Letter: Competitive intramolecular displacement of the neutral amide group. Rearrangement and dehydration reactions of asparagine and glutamine.

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Modified DNA aptamer that binds the (R)-isomer of a thalidomide derivative with high enantioselectivity

A thalidomide-binding aptamer was produced by systematic evolution of ligands by exponential enrichment from a library of non-natural DNA in which thymidine had been replaced with a modified deoxyuridine bearing a cationic functional group via a hydrophobic methylene linker at the C5 position. The additional functional group in the modified DNA aptamer could improve stability against nucleases and increase the binding affinity to thalidomide. The selected aptamer could recognize thalidomide enantioselectively, although a racemic thalidomide-attached gel was used for the selection. Surface plasmon resonance and fluorescence titration studies revealed that the selected modified DNA aptamer and a truncated version bound with an (R)-thalidomide derivative with high enantioselectivity, but not with the (S)-form. The modified group in the DNA aptamer is indispensable for the interaction with thalidomide, as the corresponding natural type DNA bearing the same base sequence showed no binding affinity with (R)-nor (S)-thalidomide. Computational sequence analysis suggested that the selected apatamer (108mer) could fold into a three-way junction structure; however, truncation of this aptamer (31 mer) revealed that the thalidomide-binding site is a hairpin-bulge region that is a component of one of the arms of the three-way junction structure. The Kd value of the truncated 31 mer aptamer for binding with the (R)-thalidomide derivative was 1.0 μM estimated from fluorescence titration study. The aptamer that can recognize a single enantiomer of thalidomide will be useful as a biochemical tool for the analysis and study of the biological action of thalidomide enantiomers.

PROCESS FOR THE PREPARATION OF POMALIDOMIDE

The present invention relates to a process for the preparation of pomalidomide. The present invention also provides a process for the preparation of 2-(2,6-dioxopiperidin-3-yl)-4-nitro-1H-isoindole-1,3(2H)-dione, a compound of Formula II and its use for the preparation of pomalidomide. The pomalidomide may be made having a yield greater than 97% and the 2-(2,6-dioxopiperidin-3-yl)-4-nitro-1H-isoindole-1,3(2H)-dione (Formula II) may be made having a yield greater than 88%.

Preparation method of deuterated intermediate

The present invention provides a preparation method of a deuterated intermediate. The deuterated intermediate has a structure shown by a formula I; the preparation method comprises the following steps: amino groups in a raw material A and an aldehyde grou