75266-38-5

Basic information

• Product Name: L-Vinylglycine hydrochloride
• Synonyms: L-Vinylglycine hydrochloride;(S)-2-AMinobut-3-enoic acid hydrochloride
• CAS NO: 75266-38-5
• Molecular Formula: C₄H₈NO₂*Cl
• Molecular Weight: 137.56482
• Mol File: 75266-38-5.mol

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: L-Vinylglycine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: L-Vinylglycine hydrochloride(75266-38-5)
• EPA Substance Registry System: L-Vinylglycine hydrochloride(75266-38-5)

Safety Data

• Hazardous Substances Data: 75266-38-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
L-Vinylglycine hydrochloride is used as a reagent for the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides due to its ability to form a wide range of chemical compounds.
Used in the Preparation of Modified Amino Acids:
L-Vinylglycine hydrochloride is utilized in the preparation of modified amino acids, enhancing their properties and expanding their applications in different fields.
Used in the Production of Biodegradable Polymers:
L-Vinylglycine hydrochloride is employed in the production of biodegradable polymers, offering an environmentally friendly alternative to traditional plastics and contributing to the development of sustainable materials.
Used as a Precursor in the Preparation of Chiral Building Blocks:
L-Vinylglycine hydrochloride is used as a precursor in the preparation of chiral building blocks, playing a crucial role in the synthesis of enantiomerically pure compounds, which are essential in various chemical and pharmaceutical applications.

Upstream product

• 104523-58-2 (S)-benzyl 2-((tert-butoxycarbonyl)amino)but-3-enoate 
• 91028-45-4 (S)-N-Phthaloylvinylglycine methyl ester 
• 119397-04-5 N-benzyloxycarbonyl-L-vinylglycine, isopropyl ester 
• 75266-42-1 (S)-2-<(benzyloxycarbonyl)amino>-3-butenoic acid 
• 90292-75-4 (S)-3-Benzyloxycarbonyl-5-oxo-4-vinyltetrahydro-1,3-oxazole 
• 75266-40-9 N-benzyloxycarbonyl-L-α-vinylglycine methyl ester 

Downstream Products

• 75266-42-1 (S)-2-<(benzyloxycarbonyl)amino>-3-butenoic acid 
• 1025434-04-1 (S)-N-(Fmoc)vinylglycine 
• 91028-43-2 (S)-vinylglycine 
• 91028-42-1 (S)-N-<(3,5-dinitrobenzyl)oxycarbonyl>vinylglycine 
• 91028-39-6 L-2-<<(tert-Butyloxy)carbonyl>amino>-3-butenoic Acid 

Relevant articles and documents

Radical-Mediated Acyl Thiol-Ene Reaction for Rapid Synthesis of Biomolecular Thioester Derivatives

The thiol-ene ‘click’ reaction has emerged as a versatile process for carbon–sulfur bond formation with widespread applications in chemical biology, medicinal chemistry and materials science. Thioesters are key intermediates in a wide range of synthetic and biological processes and efficient methods for their synthesis are of considerable interest. Herein, we report the first examples of acyl-thiol-ene (ATE) for the synthesis of biomolecular thioesters, including peptide, lipid and carbohydrate derivatives. A key finding is the profound effect of the amino acid side chain on the outcome of the ATE reaction. Furthermore, radical generated thioesters underwent efficient S-to-N acyl transfer and desulfurisation to furnish ‘sulfur-free’ ligation products in an overall amidation process with diverse applications for chemical ligation and bioconjugation.

Macrocyclic cysteine protease inhibitors and compositions thereof

The present invention provides a novel class of macrocyclic compounds, which are useful as cysteine protease inhibitors. Also provided are novel intermediates and methods of preparing the compounds. The invention also provides pharmaceutical compositions

Photochemical transformations of proteinogenic and non-proteinogenic amino acids

The photochemistry of N-activated enantiomerically pure α-amino acids is described with emphasis on chemo-, regio-, stereo-, and spin selectivity. An especially valuable chromophore is the phthalimido group. The first excited singlet states are short-lived and deactivated (chemically) via homolytic CH cleavage or (physically) via electron-transfer steps. The first excited triplet states are chemically deactivated via electron-transfer reactions and subsequent deprotonation/coupling steps. A wide variety of product types were synthesized, and potential target molecules were available by tuning the reaction conditions. Also remote groups can be activated by means of electron-transfer steps, which represents an attractive new synthetic protocol for macrocyclization.

A Photochemical Route to Vinylglycine and a Vinylglycine Dipeptide

Enantiomerically pure vinylglycine (4b) can be prepared from natural ("chiral pool") amino acids by photoelimination of γ-functionalized N-phthaloyl amino acid esters.Two routes have been developed: (a) a three-step synthesis of substrate 3b from (S)-methionine and subsequent photolysis, (b) the use of N-phthaloyl activated methyl 2-amino-4-chloro- or -4-bromo-butanoates 3d,e which are available from (S)-methionine (four-step synthesis) or from (S)-homoserine (two-step synthesis).The photoelimination (of HOSMe from 3b and of HX from 3d,e) proceeds quantitatively and leads to N,C-protected vinylglycine 4a in high yields.This strategy could also be applied to peptide-bound substrates as was shown for the protected Met-Gly (5b) which was transformed into the N-protected vinylglycineglycine dipeptide 6 in three steps. - Keywords: Vinylglycine; Photoelimination; Norrish-II photoreaction; Dipeptide; Peptide modification, photochemical

Syntheses of optically active, protected and unprotected vinylglycines

Vinylglycine (2) has been shown to undergo racemization under acidic conditions. Optically pure 2 was obtained from 2 · HCl by enzymatic hydrolysis through N-acetylvinylglycine (5), followed by recrystallization. (S)N-(Methoxycarbonyl)vinylglycine (6) was configurationally so unstable under acidic conditions that 6 could not be obtained from 2 in an optically pure form. On the other hand, configurationally stable (S)-N-(9-phenylfluoren-9-yl)vinylglycine methyl ester (9) was synthesized from (S)-homoserine; 9 was hydrolyzed with sodium hydroxide to afford the carboxylic acid 10 of more than 99% ee.

Synthesis of 3-β-D-Ribofuranosylwybutine, the Most Probable Structure for the Hypermodified Nucleoside Isolated from Yeast Phenylalanine Transfer Ribonucleic Acids

An alternative synthesis of the key intermediate 8 for the synthesis of wybutine 1 has been attained through the Heck reaction between (S)-N-(methoxycarbonyl)vinylglycine 13 and 1-benzyl-7-iodowye 7.The nucleoside version of this method using 7-iodo-3-(2,

Palladium-catalyzed heck couplings of L-vinylglycine derivatives with vinyl and aryl halides and triflates

The coupling of aryl and vinyl halides and triflates with L-vinylglycine derivatives under the influence of a palladium catalyst is described. The coupling is regioselective and stereoselective with the absolute configuration of the α-amino acid centre be

L-VINYLGLYCINE FROM L-HOMOSERINE

A simple and practical synthesis of L-vinylglycine starting from L-homoserine is described.

THE FREE RADICAL CHEMISTRY OF CARBOXYLIC ESTERS OF 2-SELENOPYRIDINE-N-OXIDE: A CONVENIENT SYNTHESIS OF (L)-VINYLGLYCINE

Optically pure (L)-vinylglycine has been synthesised by two different methods.The first of these involves protected (L)-glutamate esters of N-hydroxy-2-seleno-pyridine.Such esters are shown to undergo the same decarboxylative rearrangement as their thio-a

A NOVEL AND EFFICIENT SYNTHESIS OF L-VINYLGLYCINE

A simple and practical synthesis of the title compound starting with L-glutamic acid is described.