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421723

Sigma-Aldrich

Z-L-Phenylalaninol

97%

Synonym(s):

(S)-(−)-2-(Carbobenzyloxyamino)-3-phenyl-1-propanol, (S)-2-(Z-Amino)-3-phenyl-1-propanol, N-(Carbobenzyloxy)-L-phenylalaninol

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About This Item

Linear Formula:
C6H5CH2CH(NHCO2CH2C6H5)CH2OH
CAS Number:
6372-14-1
Molecular Weight:
285.34
Beilstein/REAXYS Number:
2816420
MDL number:
MFCD00191138
UNSPSC Code:
12352209
PubChem Substance ID:
24866399
NACRES:
NA.22

assay

97%

optical activity

[α]20/D −30°, c = 1 in chloroform

reaction suitability

reaction type: solution phase peptide synthesis

mp

90-92 °C (lit.)

application(s)

peptide synthesis

SMILES string

OC[C@H](Cc1ccccc1)NC(=O)OCc2ccccc2

InChI

1S/C17H19NO3/c19-12-16(11-14-7-3-1-4-8-14)18-17(20)21-13-15-9-5-2-6-10-15/h1-10,16,19H,11-13H2,(H,18,20)/t16-/m0/s1

InChI key

WPOFMMJJCPZPAO-INIZCTEOSA-N

Application

Employed in the synthesis of biochemically active compounds. Building block for the synthesis of HIV protease inhibitors.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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
Aldrichimica Acta, 28, 13-13 (1995)
Liu, C. et al.
Organic Process Research & Development, 1, 45-45 (1997)
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
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