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190357

(R)-(−)-2-Phenylglycinol

Name: (<I>R</I>)-(−)-2-Phenylglycinol
Brand: ALDRICH

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

Certificates of Analysis (COA)

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Tetrahedron Letters, 45, 5287-5287 (2004)

Amedjkouh, M.; Westerlund, K.

Tetrahedron Letters, 45, 5175-5175 (2004)

Straightforward synthesis of (S)- and (R)-alpha-trifluoromethyl proline from chiral oxazolidines derived from ethyl trifluoropyruvate.

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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