106572-02-5

Basic information

• Product Name: N-(N-tert-butoxycarbonyl-DL-phenylalanyl)-glycine methyl ester
• Synonyms: N-(N-tert-butoxycarbonyl-DL-phenylalanyl)-glycine methyl ester
• CAS NO: 106572-02-5
• Molecular Weight: 336.388
• Mol File: 106572-02-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(N-tert-butoxycarbonyl-DL-phenylalanyl)-glycine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(N-tert-butoxycarbonyl-DL-phenylalanyl)-glycine methyl ester(106572-02-5)
• EPA Substance Registry System: N-(N-tert-butoxycarbonyl-DL-phenylalanyl)-glycine methyl ester(106572-02-5)

Safety Data

• Hazardous Substances Data: 106572-02-5(Hazardous Substances Data)

Usage

Description

N-(N-tert-butoxycarbonyl-DL-phenylalanyl)-glycine methyl ester is a chemical compound widely utilized in the fields of organic chemistry and peptide synthesis. It is a methyl ester derivative of the dipeptide N-(tert-butoxycarbonyl-DL-phenylalanyl)-glycine, featuring a tert-butoxycarbonyl (Boc) protective group that shields the amino group of the phenylalanine residue. N-(N-tert-butoxycarbonyl-DL-phenylalanyl)-glycine methyl ester is valued for its stability and ease of manipulation, making it a preferred starting material for the synthesis of various peptide derivatives.

Uses

Used in Pharmaceutical Synthesis:
N-(N-tert-butoxycarbonyl-DL-phenylalanyl)-glycine methyl ester is used as a building block for the synthesis of pharmaceuticals and bioactive peptides. Its Boc-protected form allows for selective deprotection of the amino group under mild conditions, which is crucial for the development of complex peptide structures with specific biological activities.
Used in Organic Chemistry:
In the realm of organic chemistry, N-(N-tert-butoxycarbonyl-DL-phenylalanyl)-glycine methyl ester serves as a versatile starting material for the synthesis of a range of peptide derivatives. Its stability and the ease with which it can be manipulated make it an attractive option for researchers working on the design and synthesis of novel compounds with potential applications in various industries.
Used in Peptide Chemistry:
N-(N-tert-butoxycarbonyl-DL-phenylalanyl)-glycine methyl ester is employed as a key component in peptide chemistry, where its Boc-protected form enables selective deprotection of the amino group. This selective deprotection is essential for the synthesis of peptides with specific sequences and functions, contributing to the development of new drugs and bioactive molecules.

Upstream product

• 4530-18-1 2-(tert-butoxycarbonylamino)-3-phenylpropionic acid 
• 102-82-9 tributyl-amine 
• 79-22-1 methyl chloroformate 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 74293-09-7 2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester 
• 35909-82-1 2,3,4,6-tetra-O-benzyl-1-O-(N-tert-butoxycarbonyl-L-phenylalanyl)-β-D-glucopyranose 

Downstream Products

• 10125-07-2 3-benzyl-piperazine-2,5-dione 
• 4294-26-2 phenylalanylglycine 
• 4530-39-6 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanamido)acetic acid 

Relevant articles and documents

Piperazine Compounds Whith a Herbicidal Action

The present invention relates to piperazine compounds of the general formula I defined below and to their use as herbicides. Moreover, the invention relates to compositions for crop protection and to a method for controlling unwanted vegetation. In formula I, the variables have the following meanings: R1 is selected from the group consisting of halogen, cyano, nitro, Z—C(═O)—R11, phenyl and a 5- or 6-membered heterocyclic radical which has 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S as ring atoms, where phenyl and the heterocyclic radical are unsubstituted or may have 1, 2, 3 or 4 substituents R1a; Z is a covalent bond or a CH2 group;R11 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C5-C6-cycloalkenyl, C2-C6-alkynyl and the like;R2 is hydrogen, halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C1-C4-alkoxy, C1-C4-haloalkoxy, benzyl or a group S(O)nR21 in which R21 is C1-C4-alkyl or C1-C4-haloalkyl and n is 0, 1 or 2;R3 is hydrogen or halogen;R4 is C1-C4-alkyl, C3-C4-alkenyl or C3-C4-alkynyl; R5 is hydrogen, C1-C4-alkyl, C3-C4-alkenyl, C3-C4-alkynyl or a group C(═O)R51 in which R51 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;R6 is C1-C4-alkyl, C1-C4-hydroxyalkyl or C1-C4-haloalkyl;R7, R8 independently of one another are hydrogen, OH, C1-C4-alkoxy, C1-C4-haloalkyloxy, C1-C4-alkyl or C1-C4-haloalkyl; andR9, R10 independently of one another are selected from the group consisting of hydrogen, halogen, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C1-C4-alkoxy and C1-C4-haloalkoxy.

PEPTIDE BOND FORMATION BY INTERMOLECULAR AMINOLYSIS OF D-GLUCOPYRANOSYL ESTERS OF AMINO ACIDS

The reaction of HO-protected and -unprotected D-glucopyranosyl esters of N-acylamino acids (Gly, Ala, Phe) with glycine and phenylalanine methyl esters in N,N-dimethylformamide at 38 deg C and dichloromethane at 40 deg C, respectively, led to repture of the C-1 ester bond and formation of the corresponding N-acyldipeptide methyl ester.The relative reactivity of the C-1 ester bond toward aminolysis was greatly influenced by the structure of the amino acid nucleophile, the nature of the aglycon side-chain group, and the anomeric configuration of the D-glucopyranosyl ester involved.Evidence for a substantially lower acylating efficiency of the ester at C-2, as compared to that at C-1, was obtained by aminolysis of two fully acetylated 2-O-(acylaminoacyl)-β-D-glucopyranoses.Treatment of 1-O-(glycylglycylglycyl)-β-D-glucopyranose with phenylalanine methyl ester in N,N-dimethylformamide led to parallel hydrolysis and intermolecular aminolysis, to give the tripeptide and tetrapeptide methyl ester.