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
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Assay:
99%
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
SMILES string
[H][C@@]1(CO1)[C@H](Cc2ccccc2)NC(=O)OC(C)(C)C
InChI key
NVPOUMXZERMIJK-QWHCGFSZSA-N
assay
99%
optical activity
[α]23/D −7°, c = 0.6 in methanol
mp
125-127 °C (lit.)
functional group
amine, ether, phenyl
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.
signalword
Warning
hcodes
pcodes
Hazard Classifications
Aquatic Acute 1 - Aquatic Chronic 1
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Arun K Ghosh et al.
Journal of medicinal chemistry, 49(17), 5252-5261 (2006-08-18)
Structure-based design and synthesis of novel HIV protease inhibitors are described. The inhibitors are designed specifically to interact with the backbone of HIV protease active site to combat drug resistance. Inhibitor 3 has exhibited exceedingly potent enzyme inhibitory and antiviral
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)
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)
Novel arylsulfonamides possessing sub-picomolar HIV protease activities and potent anti-HIV activity against wild-type and drug-resistant viral strains
Miller JF, et al.
Bioorganic & Medicinal Chemistry Letters, 14(4), 959-963 (2004)
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)
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