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190357

Sigma-Aldrich

(R)-(−)-2-Phenylglycinol

98%, for peptide synthesis

Synonym(s):

(R)-2-Amino-2-phenylethanol, D-(−)-α-Phenylglycinol

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About This Item

Linear Formula:
C6H5CH(NH2)CH2OH
CAS Number:
56613-80-0
Molecular Weight:
137.18
Beilstein:
2935848
EC Number:
260-287-5
MDL number:
MFCD00008062
UNSPSC Code:
12352209
PubChem Substance ID:
24851431
NACRES:
NA.22

product name

(R)-(−)-2-Phenylglycinol, 98%

Assay

98%

optical activity

[α]24/D −31.7°, c = 0.76 in 1 M HCl

optical purity

ee: 99% (GLC)

reaction suitability

reaction type: solution phase peptide synthesis

mp

75-77 °C (lit.)

application(s)

peptide synthesis

SMILES string

N[C@@H](CO)c1ccccc1

InChI

1S/C8H11NO/c9-8(6-10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2/t8-/m0/s1

InChI key

IJXJGQCXFSSHNL-QMMMGPOBSA-N

Application

Amino alcohol used to prepare a chiral imine or oxazolidine from ethyl trifluoropyruvate. These intermediates were then employed in a synthesis of both enantiomers of α-trifluoromethylproline.
Chiral β−amino alcohol used as a synthetic building block.

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
STBK5657
STBH9185
STBH0838
STBG2103V
STBG0400V

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Sigma-Aldrich

298417

(R)-(−)-Leucinol

Tetrahedron Letters, 45, 5287-5287 (2004)
Amedjkouh, M.; Westerlund, K.
Tetrahedron Letters, 45, 5175-5175 (2004)
Grégory Chaume et al.
Organic letters, 8(26), 6123-6126 (2006-12-15)
[Structure: see text] A concise synthesis of both enantiomers of alpha-Tfm-proline and (S)-alpha-Tfm-prolinol from ethyl trifluoropyruvate is reported. The key step is a diastereoselective allylation reaction of ethyl trifluoropyruvate and (R)-phenylglycinol-based oxazolidines or imine. The lactone obtained by cyclization of

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