Cas no 128018-44-0 ((2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane)

(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane is a chiral epoxide derivative widely utilized in asymmetric synthesis and pharmaceutical intermediates. Its stereospecific (2S,3S) configuration ensures high enantioselectivity, making it valuable for constructing complex molecular architectures. The presence of the Cbz (carbobenzyloxy) protecting group enhances stability during synthetic transformations while allowing selective deprotection under mild conditions. This compound is particularly useful in peptidomimetics and bioactive molecule synthesis due to its reactive epoxide moiety and phenylbutane backbone. Its well-defined stereochemistry and functional group compatibility make it a versatile building block for medicinal chemistry and fine chemical applications. Proper handling under inert conditions is recommended to preserve its reactivity and stereochemical integrity.
(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane structure
128018-44-0 structure
Product Name:(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane
CAS No:128018-44-0
MF:C18H19NO3
MW:297.348365068436
CID:63915
PubChem ID:9861019
Update Time:2025-11-02

(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane Chemical and Physical Properties

Names and Identifiers

    • (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane
    • (2S,3S)-1,2-Epoxy-3-(benzyloxycarbonyl-amino)-4-phenylbutane
    • (1S,1'S)-1-(1'-N-benzyloxycarbonylamino-2'-phenyl)ethyloxirane
    • (1S,2S)-1-(N-benzyloxycarbonyl)-amino-2-phenylethyl-oxirane
    • (1S,2S)-Cbz epoxide
    • [(1S)-1-(2S)-oxiranyl-2-phenylethyl]-carbaMic acid phenylMethyl ester
    • [S-(R*,R*)]-(1-oxiranyl-2-phenylethyl) carbamic acid phenylmethyl ester
    • erythro N-Cbz-phenylalanyl epoxide
    • N-benzyloxycarbonyl-3(S)-amino-1,2(S)-epoxy-4-phenylbutane
    • benzyl ((S)-1-((S)-oxiran-2-yl)-2-phenylethyl)carbamate
    • benzyl N-[(1S)-1-[(2S)-oxiran-2-yl]-2-phenylethyl]carbamate
    • 3(S)-[N-(benzyloxycarbonyl) amino]-1,2(S)-epoxy-4-phenylbutane
    • 3(S)-[N-(benzyloxycarbonyl)amino]-1,2(S) -epoxy-4-phenylbutane
    • Carbamic acid, N-[(1S)-1-[(2S)-2-oxiranyl]-2-phenylethyl]-, phenylmethyl ester
    • N-benzyloxycarbonyl-3 (S) -amino-1, 2 (S) -epoxy-4-phenylbutane
    • benzyl (S)-1-((S)-oxiran-2-yl)-2-phenylethyl-carbamate
    • 3(S)-[N-(benzyloxycarbonyl)amino]-1,2(S)-epoxy-4-phenylbutane
    • 3(S)-[N-(benzyloxycarbonyl)amino] -1,2(S) -epoxy-4-phenylbutane
    • 3(S)-(N-(benzyloxycarbonyl)amino]-1,2(S)-epoxy-4-phenylbutane
    • N-benzyloxycarbonyl 3(S)-amino-1,2-(S)-epoxy-4-phenylbutane
    • ((S)-1-(S)-Oxiranyl-2-phenyl-ethyl)-carbamic acid benzyl ester
    • Phenylmethyl N-[(1S)-1-[(2S)-2-oxiranyl]-2-phenylethyl]carbamate
    • BDBM50284944
    • CHEMBL298965
    • N-Cbz-3-(S)-amino-1,2-(S)-epoxy-4-phenylbutane
    • DTXSID301172108
    • N-benzyloxycarbonyl-3(S)-amino-1,2 (S) -epoxy-4-phenylbutane
    • benzyl (1S)-1-[(2S)-oxiranyl]-2-phenylethylcarbamate
    • N-benzyloxycarbonyl 3 (S)-amino-1,2-(S)-epoxy-4-phenylbutane
    • 3(S)-(benzyloxyformamido)-1,2(S)-epoxy-4-phenylbutane
    • 128018-44-0
    • N-benzyloxycarbonyl-3 (S) -amino-1,2(s) -epoxy-4-phenylbutane
    • N-benzyloxycarbonyl-3 (S)-amino-1,2(S)-epoxy-4-phenylbutane
    • N-benzyloxycarbonyl-3(S)-amino-1,2(S)-epoxy-4- phenylbutane
    • N-benzyloxycarbonyl-3(S)-amino-1,2(S)epoxy-4-phenylbutane
    • SCHEMBL2575768
    • DURMMNMFHRIMJD-DLBZAZTESA-N
    • BCP25736
    • MDL: MFCD09750967
    • Inchi: 1S/C18H19NO3/c20-18(22-12-15-9-5-2-6-10-15)19-16(17-13-21-17)11-14-7-3-1-4-8-14/h1-10,16-17H,11-13H2,(H,19,20)/t16-,17+/m0/s1
    • InChI Key: DURMMNMFHRIMJD-DLBZAZTESA-N
    • SMILES: O1C[C@@H]1[C@H](CC1C=CC=CC=1)NC(=O)OCC1C=CC=CC=1

Computed Properties

  • Exact Mass: 297.13600
  • Monoisotopic Mass: 297.13649347g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 22
  • Rotatable Bond Count: 8
  • Complexity: 348
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 3.2
  • Topological Polar Surface Area: 50.9?2

Experimental Properties

  • PSA: 50.86000
  • LogP: 3.31380

(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane Pricemore >>

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Additional information on (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane

Comprehensive Guide to (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane (CAS No. 128018-44-0): Properties, Applications, and Market Insights

(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane (CAS No. 128018-44-0) is a chiral epoxide compound widely used in pharmaceutical synthesis and organic chemistry research. This compound features a unique epoxide ring and a Cbz-protected amino group, making it a versatile intermediate for asymmetric synthesis. With the growing demand for enantioselective drugs, (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane has gained significant attention in recent years due to its role in producing optically active pharmaceuticals.

The molecular structure of (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane includes a phenylbutane backbone with an epoxy group at the 1,2-position and a Cbz (carbobenzyloxy)-protected amino group at the 3-position. This configuration provides excellent reactivity for nucleophilic ring-opening reactions, which are crucial in synthesizing complex molecules. Researchers often search for "chiral epoxide synthesis" or "Cbz-protected amino epoxides" when exploring applications of this compound in drug development.

One of the most common applications of (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane is in the synthesis of protease inhibitors and other bioactive molecules. The compound's epoxide functionality allows for selective reactions with nucleophiles, enabling the construction of stereocenters with high precision. Recent trends in pharmaceutical research, such as "targeted drug delivery" and "personalized medicine," have increased the demand for high-purity chiral building blocks like this epoxide derivative.

From a synthetic chemistry perspective, (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane serves as a key intermediate in multi-step organic transformations. Chemists frequently use it in asymmetric synthesis protocols, particularly in reactions requiring "stereocontrol" or "enantioselective catalysis." The Cbz protecting group offers stability during synthetic operations while allowing for selective deprotection when needed, making this compound valuable for complex molecule assembly.

The market for (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane has shown steady growth, driven by increasing R&D activities in pharmaceutical companies and academic institutions. Many researchers search for "buy chiral epoxide intermediates" or "CAS 128018-44-0 suppliers" when sourcing this material for their projects. Current industry trends toward "green chemistry" and "atom economy" have also influenced the synthesis and application of this compound, with manufacturers developing more efficient production methods.

Quality control is paramount when working with (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane, as its stereochemical purity directly affects downstream applications. Analytical techniques like chiral HPLC and NMR spectroscopy are commonly employed to verify the compound's enantiomeric excess and chemical identity. The pharmaceutical industry's focus on "quality by design" (QbD) principles has further emphasized the importance of rigorous characterization for such intermediates.

Storage and handling of (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane require attention to moisture sensitivity and temperature control. While not classified as hazardous under standard conditions, proper laboratory practices should be followed to maintain the compound's stability. Researchers often inquire about "epoxide compound stability" and "storage conditions for chiral intermediates" when planning their experiments with this material.

Future research directions for (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane may explore its potential in novel synthetic methodologies and drug discovery programs. Emerging areas like "biocatalysis" and "continuous flow chemistry" could offer new approaches to utilizing this chiral building block more efficiently. As the pharmaceutical industry continues to prioritize "chiral drug development," the significance of well-characterized intermediates like (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane will likely increase.

In summary, (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane (CAS No. 128018-44-0) represents an important tool for synthetic chemists working in pharmaceutical research and development. Its unique structural features and synthetic versatility make it valuable for constructing complex molecules with precise stereochemistry. As research trends continue to emphasize "enantioselective synthesis" and "chiral technology," this compound will remain relevant in advancing medicinal chemistry and drug discovery efforts.

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