Cas no 57224-63-2 ((2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate)

(2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate is a chiral ester derivative widely utilized in organic synthesis and pharmaceutical research. Its stereochemically defined structure, featuring both (2S) and (3R) configurations, makes it a valuable intermediate for the preparation of enantiomerically pure compounds, particularly β-hydroxy-α-amino acids and their derivatives. The benzyloxycarbonyl (Cbz) protecting group ensures selective deprotection under mild conditions, enhancing its utility in peptide synthesis. The compound’s high purity and well-characterized stereochemistry contribute to its reliability in asymmetric synthesis and medicinal chemistry applications. Its stability under standard storage conditions further supports its use in complex multi-step synthetic routes.
(2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate structure
57224-63-2 structure
Product Name:(2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate
CAS No:57224-63-2
MF:C13H17NO5
MW:267.277784109116
MDL:MFCD00038585
CID:57090
PubChem ID:24865579
Update Time:2025-11-02

(2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate Chemical and Physical Properties

Names and Identifiers

    • N-Cbz-L-threonine methyl ester
    • Z-Thr-OMe
    • Z-L-Threonine methyl ester
    • N-Carbobenzyloxy-L-threonine methyl ester
    • CBZ-L-THREONINE METHYL ESTER
    • Cbz-Thr-OMe
    • L-carbobenzylolxy-L-threonine methyl ester
    • N-CARBOBENZOXY-L-THREONINE METHYL ESTER
    • N-CBz-Threo-OMe
    • Z-L-Thr-OMe
    • Z-THREONINE-OME
    • (2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate
    • OPZWAOJFQFYYIX-KOLCDFICSA-N
    • C29H32N2O4
    • N-Alpha-Carbobenzoxy-L-Threonine Methyl Ester
    • KM0077
    • 5855AE
    • 8403AB
    • AM82256
    • N-(Benzyloxycarbon
    • MDL: MFCD00038585
    • Inchi: 1S/C13H17NO5/c1-9(15)11(12(16)18-2)14-13(17)19-8-10-6-4-3-5-7-10/h3-7,9,11,15H,8H2,1-2H3,(H,14,17)/t9-,11+/m1/s1
    • InChI Key: OPZWAOJFQFYYIX-KOLCDFICSA-N
    • SMILES: O[C@H](C)[C@@H](C(=O)OC)NC(=O)OCC1C=CC=CC=1

Computed Properties

  • Exact Mass: 267.11100
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 7
  • Complexity: 301
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 2
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • XLogP3: 1.1
  • Topological Polar Surface Area: 84.9

Experimental Properties

  • Color/Form: Not available
  • Density: 1.2100 (rough estimate)
  • Melting Point: 92-94?°C (lit.)
  • Boiling Point: 444.7℃ at 760 mmHg
  • Refractive Index: 1.4365
  • Water Partition Coefficient: miscible
  • PSA: 84.86000
  • LogP: 1.22610
  • Solubility: Not available
  • Specific Rotation: -18 o (c=1, MeOH)
  • Optical Activity: [α]25/D ?18°, c =?1 in methanol

(2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate Security Information

  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • Safety Instruction: S24/25
  • Safety Term:S24/25

(2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate Customs Data

  • HS CODE:2924299090
  • Customs Data:

    China Customs Code:

    2924299090

    Overview:

    2924299090. Other cyclic amides(Including cyclic carbamates)(Including their derivatives as well as their salts). VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to, packing

    Summary:

    2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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(2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate Production Method

(2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate Suppliers

Amadis Chemical Company Limited
Gold Member
Audited Supplier Audited Supplier
(CAS:57224-63-2)(2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate
Order Number:A831347
Stock Status:in Stock
Quantity:500g
Purity:99%
Pricing Information Last Updated:Monday, 2 September 2024 15:22
Price ($):237.0

(2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate Related Literature

  • 1. High yielding synthesis of dehydroamino acid and dehydropeptide derivatives
    Paula M. T. Ferreira,Hernani L. S. Maia,Luís S. Monteiro,Joana Sacramento J. Chem. Soc. Perkin Trans. 1 1999 3697
  • 2. Stepwise oxidation of Z-threonyl- and Z-seryl-glycine esters and related compounds
    Virgilio Giormani,Fernando Filira,Ferruccio D'Angeli J. Chem. Soc. Perkin Trans. 1 1984 2721
  • 3. Polypeptides. Part XII. The preparation of 2-pyridyl esters and their use in peptide synthesis
    A. S. Dutta,J. S. Morley J. Chem. Soc. C 1971 2896
  • 4. Synthesis of glycosyltyrosine building blocks for solid-phase glycopeptide assembly: use of aryl tert-butyl ethers as glycosyl acceptors in aromatic glycosylations
    Antonio Vargas-Berenguel,Morten Meldal,Hans Paulsen,Knud J. Jensena,Klaus Bock J. Chem. Soc. Perkin Trans. 1 1994 3287

Additional information on (2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate

Exploring the Versatile Applications of (2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate (CAS No. 57224-63-2)

(2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate (CAS No. 57224-63-2) is a chiral compound that has garnered significant attention in the fields of pharmaceutical synthesis and organic chemistry. This ester derivative, characterized by its hydroxybutanoate backbone and benzyloxycarbonyl protecting group, serves as a crucial intermediate in the synthesis of complex molecules. Its unique stereochemistry and functional groups make it a valuable building block for researchers and industrial applications alike.

The compound's chiral purity and stereospecific reactivity are particularly noteworthy. With the increasing demand for enantiomerically pure pharmaceuticals, (2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate plays a pivotal role in asymmetric synthesis. Its hydroxy and carbamate functionalities allow for diverse chemical transformations, enabling the construction of biologically active molecules with high precision. This aligns with the growing trend in drug development towards targeted therapies and personalized medicine.

Recent advancements in peptide synthesis and prodrug design have further highlighted the importance of this compound. The benzyloxycarbonyl (Cbz) group serves as a protective moiety for amines, a feature extensively utilized in the stepwise assembly of peptides. Moreover, the methyl ester functionality offers additional versatility, allowing for further modifications under mild conditions. These attributes make it an indispensable tool for chemists working on cutting-edge therapeutic agents.

From an industrial perspective, the scalability of (2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate production has been optimized to meet the needs of large-scale pharmaceutical manufacturing. The compound's stability under various conditions and its compatibility with green chemistry principles contribute to its widespread adoption. As sustainability becomes a key concern in chemical production, the efficient synthesis and application of such intermediates gain even more significance.

The analytical characterization of 57224-63-2 typically involves advanced techniques such as chiral HPLC, NMR spectroscopy, and mass spectrometry. These methods ensure the high purity and correct stereochemical configuration required for its applications. Quality control measures are particularly stringent when the compound is used in pharmaceutical contexts, reflecting the industry's commitment to safety and efficacy.

In the context of current research trends, (2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate has found applications in the development of novel antiviral agents and enzyme inhibitors. The COVID-19 pandemic has accelerated research into antiviral compounds, and chiral intermediates like this one play a crucial role in such endeavors. Additionally, its utility in creating protease inhibitors positions it as valuable in addressing various viral infections.

The future prospects for CAS 57224-63-2 appear promising, with potential applications emerging in areas such as targeted drug delivery systems and smart materials. The compound's ability to serve as a scaffold for more complex structures makes it adaptable to various innovative uses. As biotechnology continues to advance, the demand for such specialized chiral building blocks is expected to grow significantly.

For researchers and procurement specialists seeking (2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate, understanding its storage requirements and handling precautions is essential. While not classified as hazardous under standard conditions, proper storage in cool, dry environments helps maintain its stability and shelf life. These practical considerations ensure optimal performance in downstream applications.

The global market for chiral intermediates like 57224-63-2 reflects the broader trends in pharmaceutical and specialty chemical industries. With Asia emerging as a major production hub and North America leading in research applications, the compound's commercial landscape is dynamic and geographically diverse. This distribution pattern underscores its importance across different segments of the chemical enterprise.

In conclusion, (2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate represents a fascinating example of how specialized chiral compounds enable advancements in medicine and materials science. Its unique combination of functional groups and stereochemistry makes it invaluable for contemporary chemical research and industrial applications. As science continues to push boundaries, compounds like this will undoubtedly play increasingly important roles in developing solutions to complex challenges.

Recommended suppliers
Amadis Chemical Company Limited
(CAS:57224-63-2)(2S,3R)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate
A831347
Purity:99%
Quantity:500g
Price ($):237.0
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