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Merck
CN

421723

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
UNSPSC Code:
12352209
NACRES:
NA.22
PubChem Substance ID:
24866399
MDL number:
MFCD00191138
Beilstein/REAXYS Number:
2816420

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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

SMILES string

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

InChI key

WPOFMMJJCPZPAO-INIZCTEOSA-N

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

Application

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
01712DG

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