349607
(S)-(+)-2-(Dibenzylamino)-1-propanol
99%
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About This Item
Linear Formula:
(C6H5CH2)2NCH(CH3)CH2OH
CAS Number:
Molecular Weight:
255.35
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352116
MDL number:
Assay:
99%
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
SMILES string
C[C@@H](CO)N(Cc1ccccc1)Cc2ccccc2
InChI key
IEEFFKXJADVWJO-HNNXBMFYSA-N
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
Application
Building block for the synthesis of HIV protease inhibitors.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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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
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
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
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
Liu, C. et al.
Organic Process Research & Development, 1, 45-45 (1997)
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