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Safety Information

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:
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.[1] Building block for the synthesis of HIV protease inhibitors.[2][3][4][5][6][7]

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

421723-5G:
421723-1G:
421723-BULK:
421723-VAR:

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