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421731

Sigma-Aldrich

(S)-(+)-2-(Dibenzylamino)-3-phenyl-1-propanol

99%

Synonym(s):

N,N-Dibenzyl-L-phenylalaninol

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About This Item

Linear Formula:
C6H5CH2CH[N(CH2C6H5)2]CH2OH
CAS Number:
111060-52-7
Molecular Weight:
331.45
MDL number:
MFCD00191984
UNSPSC Code:
12352116
PubChem Substance ID:
24866400
NACRES:
NA.22

Assay

99%

form

solid

optical activity

[α]20/D +8.0°, c = 4 in methanol

mp

72-74 °C (lit.)

functional group

amine
hydroxyl
phenyl

SMILES string

OC[C@H](Cc1ccccc1)N(Cc2ccccc2)Cc3ccccc3

InChI

1S/C23H25NO/c25-19-23(16-20-10-4-1-5-11-20)24(17-21-12-6-2-7-13-21)18-22-14-8-3-9-15-22/h1-15,23,25H,16-19H2/t23-/m0/s1

InChI key

ZXNVOFMPUPOZDF-QHCPKHFHSA-N

Related Categories

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

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Certificates of Analysis (COA)

Lot/Batch Number
02902CG

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