7444-16-8

Usage

Uses

Used in Pharmaceutical Industry:
[(benzyloxy)carbonyl]aminoacetic anhydride (non-preferred name) is used as a synthetic intermediate for the development of various pharmaceuticals. Its role in the synthesis process is crucial, as it contributes to the formation of complex molecular structures that possess therapeutic properties.
Used in Organic Chemistry:
In the field of organic chemistry, [(benzyloxy)carbonyl]aminoacetic anhydride (non-preferred name) serves as a valuable building block for the creation of diverse organic compounds. Its anhydride nature allows for versatile reactions, enabling the synthesis of a wide range of molecules with potential applications in various industries, including materials science, agrochemicals, and specialty chemicals.

Upstream product

• 541-41-3 chloroformic acid ethyl ester 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 108-24-7 acetic anhydride 
• 141-78-6 ethyl acetate 
• 75-44-5 phosgene 
• 857554-50-8 (N-benzyloxycarbonyl-glycine )-acetic acid-anhydride 
• 71-43-2 benzene 
• 80919-01-3 C₂₂H₂₀NO₅P 
• 94989-51-2 Benzyloxycarbonylamino-acetic acid 1-oxo-1λ⁵-phospholan-1-yl ester 

Downstream Products

• 2566-19-0 CbzGlyGly 
• 6833-09-6 benzyl (2-oxo-2-(phenylamino)ethyl)carbamate 
• 1212-53-9 methyl N-benzyloxycarbonylglycinate 
• 1145-81-9 ethyl 2-(benzyloxycarbonylamino)ethanoate 
• 6169-60-4 N-benzyloxycarbonyl-N-(N-benzyloxycarbonyl-glycyl)-glycine 
• 82961-72-6 5-(N-Z-glycyl)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 125405-91-6 {(S)-2-[2-({(S)-1-[(S)-1-(2-Benzyloxycarbonylamino-acetyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carbonyl}-amino)-acetylamino]-propionylamino}-acetic acid benzyl ester 
• 126027-72-3 {(S)-2-[2-((S)-6-Benzyloxycarbonylamino-2-{[(S)-1-(2-benzyloxycarbonylamino-acetyl)-pyrrolidine-2-carbonyl]-amino}-hexanoylamino)-acetylamino]-propionylamino}-acetic acid benzyl ester 
• 81239-98-7 5-pregnene-20-one-3-spiro-2'-(3'-carbobenzyloxyglycyl-1'3'-thiazolidine) 
• 88744-51-8 Z-Gly-Pab-Ala-OTmb 
• 5276-61-9 N-Benzyloxycarbonyl-glycyl-DL-phenylalanin-ethylester 
• 5893-58-3 N-Benzyloxycarbonyl-glycyl-(N-benzyloxycarbonyl-glycyl)-dicyclohexylharnstoff 
• 319008-71-4 Z-Gly-Bip-OtBu 
• 55301-19-4 2-(2-benzyloxycarbonylamino-acetylamino)-benzoic acid 

Relevant academic research and scientific papers

PEPTIDE TURN MIMETICS

Peptide mimetics of structure X herein which (i) provide a wide range of sidechain functions at all sidechain positions, (ii) can be incorporated in a peptide sequence, (iii) can be readily synthesized and (iv) have a variety of conformations. There is also provided a novel process which can provide valuable intermediates in relation to production of peptide mimetics of structure X which intermediates have a high degree of chemo- and stereo-selectivity. Preferred mimetics include structures I, II, III, IV, V and VI.

Functional group tolerance in organocatalytic regioselective acylation of carbohydrates

(Chemical Equation Presented) Organocatalytic regioselective acylation of mono- and disaccaharides with various functionalized acid anhydrides has been developed. Acylation of octyl β-D-glucopyranoside with acid anhydrides derived from R-amino acids, cinnamic acid, and gallic acid took place at C(4)-OH with 67-94% regioselectivity in the presence of catalyst 1. Regioselective acylation of disaccharides with functionalized acid anhydrides was also achieved with 78-94% selectivity. Especially, a disaccharide with seven free hydroxy groups (X = OH, R′ = H) underwent acylation at C(4)-OH with 78% regioselectivity in the presence of 1. Thus, functional group tolerance in the regioselective acylation catalyzed by 1 was found to be high.

Novel glycine like amino acids from glyco-α-aminonitriles as building blocks for peptide synthesis

Our interest in the glycoaminocyanation reaction led us to apply this methodology to introduce amino acids on a monosaccharide using the N-terminal position. The GAAs described in this paper are characterized by having the amino and carboxylic acid functionalities on a disubstituted position of the saccharide backbone leading to α,α-disubstituted glycines. These new sugar amino acids showed a restricted conformation involving a spontaneous intramolecular cyclization between the C- and N-terminal positions during hydrolysis or hydrogenolysis to give the corresponding oxopiperazine. Tripeptide mimics were obtained by the introduction of an additional amino acid using one-pot conditions starting from these cyclic by-products under basic media. We demonstrated that these pseudo tripeptides are good candidates for extension of the peptidic scaffold and cyclization.

Synthesis of amino-acid derivatives of chrysin

Various conjugates of amino acids with chrysin in which the amino acid was bonded through the C- or N-terminus to the flavone were prepared using peptide chemistry methods (symmetric anhydrides and activated esters).

Bip: A C(α)-tetrasubstituted, axially chiral α-amino acid. Synthesis and conformational preference of model peptides

By using the recently proposed biphenyl-based, C(α)-tetrasubstituted, cyclic, axially chiral α-amino acid Bip we synthesised by solution methods a large set of model peptides, including the homo-oligomer series, to the pentamer level. All of the peptides were fully characterised and their preferred conformation was assessed in solution by means of a FT-IR absorption and 1H NMR study. Results of X-ray diffraction analyses of two Bip derivatives and a terminally protected tripeptide with the sequence -Gly-Bip-Gly- are also presented. Our findings indicate that Bip tends to support β-turn and 310-helical structures, although in short peptides the fully-extended (C5) conformation would also be populated to some extent. (C) 2000 Elsevier Science Ltd.

Amino acid derivatives of 2-R-7-hydroxy-3',4'-ethylenedioxyisoflavones

A number of 7-O-aminoacyl derivatives of isoflavones have been obtained by the interaction of 2-R-7-hydroxy-3′,4′-ethylenedioxyisoflavones with the symmetrical anhydrides of N-protected amino acids.

SYNTHESIS, CONFORMATIONAL FEATURES AND BIOLOGICAL ACTIVITY OF 3> ANTIARRHYTHMIC PEPTIDE

Synthesis of Gly-Pro-Pro-Gly-Ala-Gly3>AAP in solution has been carried out.Solvent dependent conformational distribution of 3>AAP has been studied using CD and NMr spectroscopy.The CED spectra in water, methanol and trifluoro

A KINETIC STUDY OF PHOSPHINIC CARBOXYLIC MIXED ANHYDRIDES

Using 32.4 MHz (31)P n.m.r. spectroscopy, disproportionation of a series of phosphinic carboxylic mixed anhydrides derived from protected α-amino acids has been studied both as a function of the substituents at phosphorus and structure of the α-amino acid being activated.It was found that the rates of disproportionation were insignificant from a preparative aspect compared with aminolysis at 0 deg C.

A NEW REAGENT FOR THE MEDIATION OF AMIDE BOND FORMATION IN PEPTIDE SYNTHESIS.

The potential application of 1-oxo-1-chlorophospholane (5) as a novel reagent for the in situ activation of N α-protected amino acids for use in peptide bond forming reactions has been examined.Wherever possible, 32.4 MHz 31P nuclear magnetic resonance (n.m.r.) spectroscopy was employed to follow both the formation of the intermediate phospholanic-carboxylic mixed anhydride and the subsequent aminolysis reaction.