58581-52-5

Basic information

• Product Name: benzyl N-hydroxyglycinate
• CAS NO: 58581-52-5
• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 181.1885
• Mol File: 58581-52-5.mol

Chemical Properties

• Boiling Point: 325.8°C at 760 mmHg
• Flash Point: 150.8°C
• Density: 1.219g/cm³
• Vapor Pressure: 9.17E-05mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: benzyl N-hydroxyglycinate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl N-hydroxyglycinate(58581-52-5)
• EPA Substance Registry System: benzyl N-hydroxyglycinate(58581-52-5)

Safety Data

• Hazardous Substances Data: 58581-52-5(Hazardous Substances Data)

Upstream product

• 58581-42-3 C₁₆H₁₅NO₃ 
• 30563-27-0 benzyl 2-nitroacetate 
• 100-39-0 benzyl bromide 
• 1738-68-7 Gly-OBz 
• 300843-68-9 N-Cyanomethyl glycine benzyl ester 
• 58581-42-3 N-benzylideneglycine N-oxide benzyl ester 

Downstream Products

• 161009-80-9 C₃₆H₄₃N₅O₉ 
• 655252-75-8 N-benzyloxycarbonylmethyl-N-hydroxy-succinamic acid 
• 856422-14-5 2-acetoxy-N-benzyloxycarbonylmethyl-N-hydroxy-succinamic acid 
• 655252-72-5 (but-3-enoyl-hydroxy-amino)-acetic acid benzyl ester 
• 655252-74-7 (5-hydroxymethyl-3-oxo-isoxazolidin-2-yl)-acetic acid benzyl ester 
• 655252-73-6 (5-iodomethyl-3-oxo-isoxazolidin-2-yl)-acetic acid benzyl ester 

Relevant articles and documents

5-Hydroxy[1,2]oxazinan-3-ones as potential carbapenem and D-ala-D-ala surrogates

The title compounds are amino acids whose nitrogen atom is enclosed in a six-membered cyclic hydroxamate bearing a C5-hydroxyl group. They belong to a proposed new family of antibacterial agents targeted to the penicillin receptor. The glycine and alanine members of the family have been synthesized, as racemates, in seven steps from the four-carbon synthon diketene and the tert-butyl esters of N-hydroxyglycine and N-hydroxyalanine. Numerous alternatives to diketene have also been examined, but these lead mainly to five-membered cyclic hydroxamates. The theoretical considerations that have led to this synthetic programme are discussed in some detail. They include analysis of the structures of natural and unnatural penicillin surrogates, analysis of the penicillin pharmacophore, and a treatment of the chemical reaction with which penicillin blocks bacterial cell wall synthesis. The glycine derivative exhibits marginal but real activity vs. Micrococcus luteus. The alanine derivative, which more closely resembles D-ala-D-ala, is fifty times more active. Two five-membered structural isomers of the glycine derivative are inactive.

A novel transformation of primary amines to N-monoalkylhydroxylamines

A novel transformation of primary amines to the corresponding N-monoalkylhydroxylamines is described. The three-step protocol involves selective mono-cyanomethylation of primary amines, regioselective formation of nitrones by m-CPBA oxidation, and hydroxylaminolysis of the nitrones with hydroxylamine hydrochloride. The method is applicable for a wide range of primary amines, including alkyl, benzyl, and chiral.

Peptide backbone-to-backbone cyclisation as an avenue to β-turn mimics

1,3-Dipolar cycloaddition of the nitrone functionality of 13 and the alkene functionality of 8 yields the backbone-to-backbone cyclised peptides 14-16. The conformation of these structures is such that they are p-turn mimics. They differ in their C3/C5 stereochemistry with discrete conformational differences.