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Merck
CN

476951

(2S,3S)-1,2-环氧-3-(Boc-氨基)-4-苯基丁烷

99%

别名:

[S-(R*,R*)]-(-)-(1-环氧乙基-2-苯乙基)氨基甲酸叔丁酯

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关于此项目

经验公式(希尔记法):
C15H21NO3
化学文摘社编号:
分子量:
263.33
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
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产品名称

(2S,3S)-1,2-环氧-3-(Boc-氨基)-4-苯基丁烷, 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.

pictograms

Environment

signalword

Warning

hcodes

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

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分析证书(COA)

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William P Esler et al.
Bioorganic & medicinal chemistry letters, 14(8), 1935-1938 (2004-03-31)
(Hydroxyethyl)urea peptidomimetics are potent inhibitors of gamma-secretase that are accessible in a few synthetic steps. Systematic alteration of P2-P4' revealed that the corresponding S2-S4' active site pockets accommodate a variety of substituents, consistent with the fact that this protease cleaves
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
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
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)
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)

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