40371-50-4

Basic information

• Product Name: (S)-N-Carbobenzyloxy-4-amino-2-hydroxybutyric acid
• Synonyms: L--a-Hydroxy-BenzyloxycarbonylaminoButyricAcid(CBZ-HABA);(S)-(+)-Z-4-AMINO-2-HYDROXYBUTYRIC ACID;(S)-CBZ-HABA;(S)-N-CARBOBENZYLOXY-4-AMINO-2-HYDROXYBUTYRIC ACID;(S)-(-)-GAMMA-N-CBZ-AMINO-ALPHA-HYDROXYBUTYRIC ACID;(S)-4-BENZYLOXYCARBONYLAMINO-2-HYDROXYBUTYRIC ACID;(s)-2-hydroxy-4-[[(phenylmethoxy)carbonyl]amino]butyric acid;L-(-)-ALPHA-HYDROXY-GAMMA-BENZYLOXYCARBONYLAMINO BUTYRIC ACID
• CAS NO: 40371-50-4
• Molecular Formula: C₁₂H₁₅NO₅
• Molecular Weight: 253.25
• EINECS: 254-892-3
• Product Categories: Pharmaceutical Intermediates;API intermediates;Carboxylic Acids;Chiral Building Blocks;Organic Building Blocks
• Mol File: 40371-50-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 75-78 °C(lit.)
• Boiling Point: 396.45°C (rough estimate)
• Flash Point: 269 ºC
• Appearance: off-white crystalline powder
• Density: 1.2499 (rough estimate)
• Vapor Pressure: 1.08E-11mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 3.73±0.10(Predicted)
• CAS DataBase Reference: (S)-N-Carbobenzyloxy-4-amino-2-hydroxybutyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-Carbobenzyloxy-4-amino-2-hydroxybutyric acid(40371-50-4)
• EPA Substance Registry System: (S)-N-Carbobenzyloxy-4-amino-2-hydroxybutyric acid(40371-50-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 40371-50-4(Hazardous Substances Data)

Usage

Description

(S)-N-Carbobenzyloxy-4-amino-2-hydroxybutyric acid, also known as (S)-(+)-Z-4-Amino-2-hydroxybutyric Acid, is an organic compound with the chemical formula C11H15NO4. It is an off-white crystalline powder that plays a significant role in the pharmaceutical industry due to its unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
(S)-N-Carbobenzyloxy-4-amino-2-hydroxybutyric acid is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly aminoglycoside antibiotics. These antibiotics are known for their effectiveness against a wide range of bacterial infections, making this compound a valuable asset in the development of new drugs to combat antibiotic-resistant bacteria.
Used in Chemical Research:
As a versatile organic compound, (S)-N-Carbobenzyloxy-4-amino-2-hydroxybutyric acid is also utilized in chemical research for the development of novel chemical entities and the study of various reaction mechanisms. Its unique structure allows for further functionalization and modification, enabling the creation of new molecules with potential applications in various fields, including medicine, agriculture, and materials science.

InChI:InChI=1/C12H15NO5/c14-10(11(15)16)6-7-13-12(17)18-8-9-4-2-1-3-5-9/h1-5,10,14H,6-8H2,(H,13,17)(H,15,16)/t10-/m1/s1

Upstream product

• 54755-69-0 L-(-)-4-benzyloxycarbonylamino-2-hydroxybutyric acid 
• 3938-83-8 (S)-4-amino-2-hydroxybutanoic acid 
• 501-53-1 benzyl chloroformate 
• 81323-56-0 Methyl N-benzyloxycarbonyl-4-amino-2-oxobutanoate 

Downstream Products

• 3938-83-8 (S)-4-amino-2-hydroxybutanoic acid 
• 110880-95-0 (S)-4-Benzyloxycarbonylamino-2-methoxybutyric Acid Methyl Ester 
• 40371-52-6 N-[(S)-4-benzyloxycarbonylamino-2-hydroxy-butyryloxy]succinimide 
• 849773-54-2 tert-butyl (2S)-4-{[(benzyloxy)carbonyl]amino}-2-hydroxybutanoate 
• 860795-53-5 5-O-(4-azido-3,6-dideoxy-β-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-[(S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoyl]-3,2',3'-triazidoneamine 
• 860795-48-8 6-O-(3-azido-2-O-benzyl-3,6-dideoxy-α-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-[(S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoyl]-3,2',3'-triazidoneamine 
• 860795-47-7 6-O-(4-azido-2,3-di-O-benzyl-4,6-dideoxy-α-D-glucopyranosyl)-3',4'-di-O-benzyl-1-N-[(S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoyl]-3,2',3'-triazidoneamine 
• 882050-17-1 5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-1-N-[(S)-4-(benzyloxycarbonyl-amino)-2-hydroxybutanoyl]-3,2',6'-triazido-3',4'-dideoxy-3'-enoneamine 
• 849773-58-6 (R)-4-Benzyloxycarbonylamino-2-[(biphenyl-4-sulfonyl)-isopropoxy-amino]-butyric acid 
• 849773-56-4 (R)-tert-butyl 8-(biphenyl-4-ylsulfonyl)-10-methyl-3-oxo-1-phenyl-2,9-dioxa-4,8-diazaundecane-7-carboxylate 
• 849773-60-0 C₃₃H₄₅N₃O₇SSi 
• 419573-54-9 1-N-[(S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoyl]-6-O-[2-N-(2-(benzyloxycarbonyl)ethylamino)ethylamino]-3,2',6'-tris(N-benzyloxycarbonyl)neamine 
• 419573-55-0 1-N-[(S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoyl]-6-O-[2-N-[3-(benzyloxycarbonyl)propylamino]ethylamino]-3,2',6'-tris(N-benzyloxycarbonyl)neamine 
• 419573-56-1 1-N-[(S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoyl]-6-O-[2-N-[4-(benzyloxycarbonyl)butylamino]ethylamino]-3,2',6'-tris(N-benzyloxycarbonyl)neamine 

Relevant articles and documents

Amine-Functionalized Polylactide-PEG Copolymers

The formation of halogenated carboxylic acid intermediate followed by a ring-closing reaction led to amino-functionalized asymmetrical lactide monomer. PEG-based functional diblock and triblock polylactides were synthesized via a controlled ring-opening p

Design of novel antibiotics that bind to the ribosomal acyltransfer site

The structure of neamine bound to the A site of the bacterial ribosomal RNA was used in the design of novel aminoglycosides. The design took into account stereo and electronic contributions to interactions between RNA and aminoglycosides, as well as a ran

4-O-(2,3,5-Trideoxy-5-amino-α-D-pentofuranosyl)-6-O-aminoglycosyl-1,3-diaminocyclitois, methods for their preparation, pharmaceutical formulations thereof and their use as antibacterial agents

4-O-(2,3,5-Trideoxy-5-amino-α-D-pentofuranosyl)-6-O-aminoglycosyl-1,3-diaminocyclitols and 1-N-substituted derivatives thereof are described together with methods for their preparation and their use as antibacterial agents. Preferred are 1-N-(ω-amino-α-hydroxyalkanoyl)-[4-O-(2,3,5-trideoxy-5-amino-α-D-pentofuranosyl)-6-O-garosaminyl-2-deoxystreptamines], particularly the 1-N-(S-β-amino-α-hydroxypropionyl) derivatives, which are broad spectrum antibacterial agents.