4779-31-1

Basic information

• Product Name: Z-ASP-OBZL
• Synonyms: CBZ-L-ASP-ALPHA-BENZYL ESTER;CBZ-L-ASPARTIC ACID A-BENZYL ESTER;2-Benzyloxycarbonylamino-succinic acid 1-benzyl ester;Z-L-aspartic acid α-benzyl ester;CBZ-ASP-OBZL;N-Benzyloxycarbonyl-L-aspartic acid ALPHA-benzyl ester;Z-L-ASPARTIC ACID A-BENZYLESTER;N-[(PHENYLMETHOXY)CARBONYL]-L-ASPARTIC ACID 1-(PHENYLMETHYL) ESTER
• CAS NO: 4779-31-1
• Molecular Formula: C₁₉H₁₉NO₆
• Molecular Weight: 357.36
• Product Categories: Amino Acids & Derivatives
• Mol File: 4779-31-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 83-85°C
• Boiling Point: 583.5 °C at 760 mmHg
• Flash Point: 306.7 °C
• Appearance: Colourless solid
• Density: 1.293 g/cm³
• Vapor Pressure: 1.85E-14mmHg at 25°C
• Refractive Index: 1.581
• Storage Temp.: Store at RT.
• Solubility: Acetone, Chloroform, DMSO, Ether, Methanol
• PKA: 4.09±0.19(Predicted)
• CAS DataBase Reference: Z-ASP-OBZL(CAS DataBase Reference)
• NIST Chemistry Reference: Z-ASP-OBZL(4779-31-1)
• EPA Substance Registry System: Z-ASP-OBZL(4779-31-1)

Safety Data

• Hazardous Substances Data: 4779-31-1(Hazardous Substances Data)

Usage

Description

Z-ASP-OBZL, also known as N-Carbobenzyloxy-L-aspartic Acid 1-Benzyl Ester, is a compound with the CAS number 4779-31-1. It is a colorless solid that is useful in organic synthesis. Z-ASP-OBZL is characterized by its unique chemical structure, which allows it to participate in various chemical reactions and contribute to the formation of different products.

Uses

Used in Organic Synthesis:
Z-ASP-OBZL is used as a synthetic building block for the creation of various organic compounds. Its unique structure allows it to be a versatile component in the synthesis of a wide range of molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Z-ASP-OBZL is used as an intermediate in the synthesis of various drugs. Its ability to participate in different chemical reactions makes it a valuable asset in the development of new medications with specific therapeutic properties.
Used in Agrochemical Industry:
Z-ASP-OBZL is also utilized in the agrochemical industry for the synthesis of various agrochemical products, such as pesticides and herbicides. Its role in organic synthesis allows for the creation of compounds with targeted effects on specific pests or weeds, contributing to more efficient and environmentally friendly agricultural practices.
Used in Research and Development:
In the field of research and development, Z-ASP-OBZL serves as a valuable compound for exploring new chemical reactions and understanding the underlying mechanisms. Its use in this context helps to advance the knowledge of organic chemistry and contribute to the discovery of new synthetic pathways and applications.

InChI:InChI=1/C19H19NO6/c21-17(22)11-16(18(23)25-12-14-7-3-1-4-8-14)20-19(24)26-13-15-9-5-2-6-10-15/h1-10,16H,11-13H2,(H,20,24)(H,21,22)/t16-/m0/s1

Upstream product

• 7362-93-8 (S)-3-amino-4-(benzyloxy)-4-oxobutanoic acid 
• 7621-84-3 O¹-benzyl-N-benzyloxycarbonyl-L-aspartic acid-anhydride 
• 501-53-1 benzyl chloroformate 
• 1152-61-0 N-Cbz-L-Asp 
• 4668-39-7 benzyl N^α-benzyloxycarbonyl-L-asparaginate 
• 100-39-0 benzyl bromide 
• 80452-05-7 Caesium; (S)-2-benzyloxycarbonylamino-3-tert-butoxycarbonyl-propionate 
• 100-51-6 benzyl alcohol 
• 4515-23-5 N-benzyloxycarbonyl-L-aspartic acid anhydride 
• 64578-11-6 N-(benzyloxycarbonyl)-L-aspartic acid-4-chloride-1-benzyl ester 
• 27344-79-2 sodium diisopropyl phosphite 
• 2303-76-6 sodium diethyl phosphite 
• 88966-25-0 N-benzyloxycarbonyl-L-aspartic anhydride 
• 80452-06-8 N-benzyloxycarbonyl-L-aspartic acid 1-benzyl ester 4-tert-butyl ester 

Downstream Products

• 19246-28-7 Benzyl-N-carbobenzoxy-β-L-asparagyl-L-serin 
• 20806-05-7 N-Benzyloxycarbonyl-L-asparaginsaeure-β- 
• 108325-86-6 1-benzyl N-benzyloxycarbonyl-4-(N-succinimido)-L-aspartate 
• 118380-75-9 2,3,4-tri-O-acetyl-N-<1-benzyl-N-(benzyloxycarbonyl)-L-aspart-4-oyl>-β-D-xylopyranosylamine 
• 80887-38-3 2-acetamido-4-O-allyl-3,6-di-O-benzyl-N<(S)-3-benzyloxycarbonyl-3-(benzyloxycarbonylamino)propionyl>-2-deoxy-β-D-glucopyranosylamine 
• 118534-77-3 Z-Asp-(O-1-Ada)-OBzl 
• 118534-78-4 Z-Asp-(O-2-Ada)-OBzl 
• 124921-77-3 (2S,8S)-2,8-Bis(benzyloxycarbonylamino)-4-oxo-5-azanonadisaeure-dibenzylester 
• 109276-80-4 (S)-2-Benzyloxycarbonylamino-succinic acid 1-benzyl ester 4-(2-thioxo-2H-pyridin-1-yl) ester 
• 129579-92-6 2-acetamido-4-O-(2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranosyl)-3-O-acetyl-2-deoxy-6-O-(2'',3'',4''-tri-O-acetyl-α-L-fucopyranosyl)-1-N-<1-benzyl N-(benzyloxy)carbonyl-L-aspart-4-oyl>-β-D-glucopyranosylamine 
• 77489-39-5 2,3,4,6-tetra-O-acetyl-1-N--β-D-galactopyranosylamine 
• 77437-65-1 O-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-N-(benzyl-N-benzyloxycarbonyl-L-asparthyl)-α-D-glucopyranosylamine 
• 77437-65-1 O-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-N-(benzyl-N-benzyloxycarbonyl-L-asparthyl)-β-D-glucopyranosylamine 
• 77519-80-3 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-acetyl-1-N-<1-benzyl N-(benzyloxy)carbonyl-L-aspart-4-oyl>-2-deoxy-β-D-glucopyranosylamine 

Relevant articles and documents

Manipulating L-aspartic and L-glutamic acids - Diastereoselective synthesis of enantiopure β-amino-γ-hydroxy acids and γ-amino-δ-hydroxy acids

Enantiopure (3S,4R)- and (3S,4S)-3-amino-4-hydroxyhexanoic acids and (4S,5R)- and (4S,5S)-4-amino-5-hydroxyheptanoic acid derivatives have been prepared by stereodivergent synthesis from L-aspartic and L-glutamic acids, respectively. The stereochemistry at the carbon atom attached to the amino group was determined from the starting material but the configuration at C-4 or C-5 is controlled by diastereoselective alkylation with diethylzinc or ethylmagnesium bromide. The protection of the carboxylic group as OBO orthoester improved the yields in the final products. Wiley-VCH Verlag GmbH & Co, KGaA, 69451 Weinheim, Germany, 2003.

Tetrahydro-1,3-oxazin-6-ones as templates for the stereoselective synthesis of β-substituted L-aspartic acids

Protected (4S)-4-carboxytetrahydro-1,3-oxazin-6-ones have been synthesised either by Baeyer-Villiger reaction on a 4-ketoproline derivative or, more directly, from an aspartate derivative. Two strategies have been used to develop these compounds as chiral templates in the synthesis of β-substituted aspartic acids. In the first, formation of an enaminone using Bredereck's reagent, followed by reaction with a Grignard reagent gave a series of alkylidene derivatives which could be reduced from the less hindered side by heterogeneous catalytic hydrogenation to give cis-oxazinones in a completety stereoselective manner. Alternatively, an alkylation strategy, although trans-selective, gave mixtures of isomers. The oxazinones were converted to β-substituted aspartic acids and to regioselectively protected β-substituted aspartic acids without loss of stereochemistry ar either centre.

Synthesis of Selectively Multi-Labelled Histidines with Stable Isotopes and Chiral Synthesis of L-Histidine from L-Aspartic Acid

An efficient and concise synthesis of three types of multi-labelled histidines with stable isotopes to be used for investigating pharmacokinetics and enzymic reaction mechanisms in vivo is described.Selective deuteriation at C-3 and C-5 of DL-diamino acid 4 was achieved by hydrogen exchange to give DL-diamino acid 5.The imidazole ring was constructed by heating of compound 5 with NaSC(15)N to give labelled 2'-mercapto-DL-histidine 6, which was oxidized at C-2' to give the desired L-histidine L-7 after enzymic resolution.To replace deuterium at C-5' with hydrogen, the labelled histidine was heated in water (pH 5.0) at 180 deg C, and subsequent enzymic resolution gave L-histidine L-8.A similar sequence of reactions carried out on the diamino acid 5 with KS(13)C(15)N gave DL-histidine 7-(13)C.Deuteriation at C-2 and C-2' of 7-(13)C with DCl-D2O (pD 5.0) at 180 deg C and subsequent back-exchange of deuterium at C-2' with water (pH 7.0) at 120 deg C gave DL-histidine 10.Synthesis of optically pure L-histidine starting from L-aspartic acid is also described.The optical purity of the synthesized L-histidine was estimated to be 93.8 percent (e.e).