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Sigma-Aldrich

(S)-(+)-2-(Dibenzylamino)-1-propanol

99%

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About This Item

Linear Formula:
(C6H5CH2)2NCH(CH3)CH2OH
CAS Number:
60479-65-4
Molecular Weight:
255.35
MDL number:
MFCD00191985
UNSPSC Code:
12352116
PubChem Substance ID:
24861690
NACRES:
NA.22

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.)

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

Certificates of Analysis (COA)

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Liu, C. et al.
Organic Process Research & Development, 1, 45-45 (1997)
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
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
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
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
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