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Sigma-Aldrich

Ac-Val-OH

Synonym(s):

N-α-Acetyl-L-valine, N-Acyl-Valine

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About This Item

Empirical Formula (Hill Notation):
C7H13NO3
CAS Number:
96-81-1
Molecular Weight:
159.18
EC Number:
202-537-8
MDL number:
MFCD03939895
UNSPSC Code:
12352116
PubChem Substance ID:
329769013
NACRES:
NA.22

Assay

95%

form

powder

mp

170.5 °C

application(s)

peptide synthesis

SMILES string

O=C(O)[C@H](C(C)C)NC(C)=O

InChI

1S/C7H13NO3/c1-4(2)6(7(10)11)8-5(3)9/h4,6H,1-3H3,(H,8,9)(H,10,11)/t6-/m0/s1

InChI key

IHYJTAOFMMMOPX-LURJTMIESA-N

General description

Ac-Val-OH is an N-protected valine amino acid ligand. It participates in the 2,6-diolefination reaction of phenylacetic acids.

Application

Ac-Val-OH may be employed as a ligand for the meta-selective tert-alkylation reaction.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Keary M Engle et al.
Journal of the American Chemical Society, 132(40), 14137-14151 (2010-09-22)
Initial rate studies have revealed dramatic acceleration in aerobic Pd(II)-catalyzed C-H olefination reactions of phenylacetic acids when mono-N-protected amino acids are used as ligands. In light of these findings, systematic ligand tuning was undertaken, which has resulted in drastic improvements
Jie Li et al.
Journal of the American Chemical Society, 137(43), 13894-13901 (2015-09-30)
Acylated amino acid ligands enabled ruthenium(II)-catalyzed C-H functionalizations with excellent levels of meta-selectivity. The outstanding catalytic activity of the ruthenium(II) complexes derived from monoprotected amino acids (MPAA) set the stage for the first ruthenium-catalyzed meta-functionalizations with removable directing groups. Thereby

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