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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

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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

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Certificates of Analysis (COA)

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

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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)
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
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
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