476951
(2S,3S)-1,2-Epoxy-3-(Boc-amino)-4-phenylbutane
99%
Synonym(s):
tert-Butyl [S-(R*,R*)]-(−)-(1-oxiranyl-2-phenylethyl)carbamate
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About This Item
Empirical Formula (Hill Notation):
C15H21NO3
CAS Number:
Molecular Weight:
263.33
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Assay
99%
optical activity
[α]23/D −7°, c = 0.6 in methanol
mp
125-127 °C (lit.)
functional group
amine
ether
phenyl
SMILES string
[H][C@@]1(CO1)[C@H](Cc2ccccc2)NC(=O)OC(C)(C)C
InChI
1S/C15H21NO3/c1-15(2,3)19-14(17)16-12(13-10-18-13)9-11-7-5-4-6-8-11/h4-8,12-13H,9-10H2,1-3H3,(H,16,17)/t12-,13+/m0/s1
InChI key
NVPOUMXZERMIJK-QWHCGFSZSA-N
Application
(2S,3S)-1,2-Epoxy-3-(Boc-amino)-4-phenylbutane can be used as a reactant to prepare:
- Hydroxyethyl urea peptidomimetics as potent γ-secretase inhibitors.
- Arylsufonamide derivatives.
- Peptidomimetic β-secretase inhibitors incorporating hydroxyethylamine isosteres.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Acute 1 - Aquatic Chronic 1
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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Probing pockets S2-S4? of the ?-secretase active site with (hydroxyethyl) urea peptidomimetics
Esler WP, et al.
Bioorganic & Medicinal Chemistry Letters, 14(8), 1935-1938 (2004)
John F Miller et al.
Bioorganic & medicinal chemistry letters, 14(4), 959-963 (2004-03-12)
A novel series of P1' chain-extended arylsufonamides was synthesized and evaluated for wild-type HIV protease inhibitory activity and in vitro antiviral activity against wild type virus and two protease inhibitor-resistant mutant viruses. All of the compounds showed dramatic increases in
Akbar Ali et al.
Journal of medicinal chemistry, 49(25), 7342-7356 (2006-12-08)
Here, we describe the design, synthesis, and biological evaluation of novel HIV-1 protease inhibitors incorporating N-phenyloxazolidinone-5-carboxamides into the (hydroxyethylamino)sulfonamide scaffold as P2 ligands. Series of inhibitors with variations at the P2 phenyloxazolidinone and the P2' phenylsulfonamide moieties were synthesized. Compounds
Structure-based design of novel HIV-1 protease inhibitors to combat drug resistance
Ghosh AK, et al.
Journal of medicinal chemistry, 49(17), 5252-5261 (2006)
Discovery of HIV-1 protease inhibitors with picomolar affinities incorporating N-aryl-oxazolidinone-5-carboxamides as novel P2 ligands
Ali Akbar, et al.
Journal of medicinal chemistry, 49(25), 7342-7356 (2006)
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