7444-16-8

Basic information

• Product Name: {[(benzyloxy)carbonyl]amino}acetic anhydride (non-preferred name)
• CAS NO: 7444-16-8
• Molecular Formula: C₂₀H₂₀N₂O₇
• Molecular Weight: 400.382
• Mol File: 7444-16-8.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 597.7°C at 760 mmHg
• Flash Point: 315.3°C
• Density: 1.303g/cm³
• Vapor Pressure: 3.01E-14mmHg at 25°C
• Refractive Index: 1.568
• CAS DataBase Reference: {[(benzyloxy)carbonyl]amino}acetic anhydride (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: {[(benzyloxy)carbonyl]amino}acetic anhydride (non-preferred name)(7444-16-8)
• EPA Substance Registry System: {[(benzyloxy)carbonyl]amino}acetic anhydride (non-preferred name)(7444-16-8)

Safety Data

• Hazardous Substances Data: 7444-16-8(Hazardous Substances Data)

Usage

General Description

The chemical {[(benzyloxy)carbonyl]amino}acetic anhydride, also known as N-[(benzyloxy)carbonyl]glycine anhydride, is a compound with the molecular formula C14H13NO5. It is an anhydride derivative of N-[(benzyloxy)carbonyl]glycine and is mainly used as an intermediate in the synthesis of pharmaceuticals and other organic compounds. The compound has a low water solubility and may be a potential irritant to the skin and eyes. It is important to handle and use this chemical with proper safety precautions to avoid any potential health risks.

Upstream product

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

Downstream Products

• 2566-20-3 [2-(2-Benzyloxycarbonylamino-acetylamino)-acetylamino]-acetic acid 
• 1212-53-9 methyl N-benzyloxycarbonylglycinate 
• 6169-60-4 N-benzyloxycarbonyl-N-(N-benzyloxycarbonyl-glycyl)-glycine 
• 319008-71-4 Z-Gly-Bip-OtBu 
• 152969-71-6 7-(N-carbobenzyloxyglycyloxy)-5-hydroxy-2-phenylchromen-4-one 
• 1194234-26-8 octyl 4-O-(2-benzyloxycarbonylaminoacetyl)-β-D-glucopyranoside 
• 244228-35-1 C₂₃H₃₃N₃O₈ 
• 1012796-18-7 3-C-[(benzyloxycarbonylglycyl)aminomethyl]-3-deoxy-1,2:5,6-di-O-isopropylidene-3-{[(methoxycarbonyl)methyl]amino}-α-D-allofuranose 
• 449205-67-8 (3R)-1,2:5,6-di-O-isopropylidene-spiro[3-deoxy-α-D-ribohexofuranose-3,5'-piperazine]-2'-one 
• 105820-24-4 N,N'-Bis-benzyloxycarbonyl-glycyl-glycin-anhydrid 
• 103459-52-5 N-(N-benzyloxycarbonyl-glycyl)-glycine-anhydride 
• 55301-19-4 2-(2-benzyloxycarbonylamino-acetylamino)-benzoic acid 
• 106273-40-9 3-(N-benzyloxycarbonyl-glycyloxy)-butyric acid amide 
• 5893-58-3 N-Benzyloxycarbonyl-glycyl-(N-benzyloxycarbonyl-glycyl)-dicyclohexylharnstoff 

Relevant articles and documents

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.

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.

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.