Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

476951

Sigma-Aldrich

(2S,3S)-1,2-Epoxy-3-(Boc-amino)-4-phenylbutane

99%

Synonym(s):

tert-Butyl [S-(R*,R*)]-(−)-(1-oxiranyl-2-phenylethyl)carbamate

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C15H21NO3
CAS Number:
98737-29-2
Molecular Weight:
263.33
MDL number:
MFCD02258997
UNSPSC Code:
12352005
PubChem Substance ID:
24871318
NACRES:
NA.22

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.[1][2][3]
  • Arylsufonamide derivatives.[4]
  • Peptidomimetic β-secretase inhibitors incorporating hydroxyethylamine isosteres.[5]

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P501

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKBC3134
06323MH
14317DE
08214TD
94856MD

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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)
View All Related Papers

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service