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About This Item
Linear Formula:
(C6H5CH2)2NCH(CH3)CH2OH
CAS Number:
Molecular Weight:
255.35
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Assay
99%
optical activity
[α]20/D +90°, c = 1 in chloroform
bp
142-148 °C/0.1 mmHg (lit.)
mp
46-48 °C (lit.)
functional group
amine
hydroxyl
phenyl
SMILES string
C[C@@H](CO)N(Cc1ccccc1)Cc2ccccc2
InChI
1S/C17H21NO/c1-15(14-19)18(12-16-8-4-2-5-9-16)13-17-10-6-3-7-11-17/h2-11,15,19H,12-14H2,1H3/t15-/m0/s1
InChI key
IEEFFKXJADVWJO-HNNXBMFYSA-N
Application
Building block for the synthesis of HIV protease inhibitors.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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C N Hodge et al.
Chemistry & biology, 3(4), 301-314 (1996-04-01)
Effective HIV protease inhibitors must combine potency towards wild-type and mutant variants of HIV with oral bioavailability such that drug levels in relevant tissues continuously exceed that required for inhibition of virus replication. Computer-aided design led to the discovery of
D Scholz et al.
Journal of medicinal chemistry, 37(19), 3079-3089 (1994-09-16)
A convenient procedure for the synthesis of 2-heterosubstituted statine derivatives as novel building blocks in HIV-protease inhibitors has been developed. The synthesis starts with protected L-phenylalaninols, which were converted to gamma-amino alpha, beta-unsaturated esters in a one-pot procedure. A highly
P Y Lam et al.
Journal of medicinal chemistry, 39(18), 3514-3525 (1996-08-30)
High-resolution X-ray structures of the complexes of HIV-1 protease (HIV-1PR) with peptidomimetic inhibitors reveal the presence of a structural water molecule which is hydrogen bonded to both the mobile flaps of the enzyme and the two carbonyls flanking the transition-state
Michael E. Pierce et al.
The Journal of organic chemistry, 61(2), 444-450 (1996-01-26)
DMP 323, a potent HIV-1 protease inhibitor, has been synthesized by an efficient stereoselective process, amenable to large scale preparations. The core C(2) symmetric diol was synthesized by a stereoselective pinacol coupling of CBZ protected D-phenylalanine. Judicious selection of protecting
Pierre L. Beaulieu et al.
The Journal of organic chemistry, 61(11), 3635-3645 (1996-05-31)
Enantiomerically pure N,N-dibenzyl-alpha-amino aldehydes reacted with (chloromethyl)lithium, generated in situ from bromochloromethane and lithium metal, to give predominantly erythro aminoalkyl epoxides. Treatment of the crude epoxides with aqueous hydrochloric acid gave crystalline (2S,3S)-N,N-dibenzylamino chlorohydrin hydrochlorides in 32-56% overall yield and
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