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68193

Sigma-Aldrich

Methyl L-3-phenyllactate

≥97.0% (HPLC)

Synonym(s):

Methyl (S)-2-hydroxy-3-phenylpropionate

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About This Item

Empirical Formula (Hill Notation):
C10H12O3
CAS Number:
13673-95-5
Molecular Weight:
180.20
MDL number:
MFCD00038224
UNSPSC Code:
12352108
PubChem Substance ID:
57652130
NACRES:
NA.22

Assay

≥97.0% (HPLC)

optical activity

[α]/D +4.4±0.5°, c = 1% in methanol

mp

40-45 °C (lit.)

functional group

ester
hydroxyl
phenyl

SMILES string

COC(=O)[C@@H](O)Cc1ccccc1

InChI

1S/C10H12O3/c1-13-10(12)9(11)7-8-5-3-2-4-6-8/h2-6,9,11H,7H2,1H3/t9-/m0/s1

InChI key

NMPPJJIBQQCOOI-VIFPVBQESA-N

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Application

Methyl L-3-phenyllactate can be used:
  • As an intermediate in the synthesis of bortezomib analogs as 20S proteasome inhibitors.
  • As a substrate in the amination of the benzylic C-H bonds and the aminated products are further used to prepare β-lactams.
  • As an intermediate in one of the key synthetic steps for the preparation of YM-254890 analog, a selective Gαq/11 inhibitor.

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
BCBM8630V
1299674V
1299674
1368259
1068074

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Discovery of novel 20S proteasome inhibitors by rational topology-based scaffold hopping of bortezomib
Xu Y, et al.
Bioorganic & Medicinal Chemistry Letters, 28(12), 2148-2152 (2018)
Toward the selective inhibition of G proteins: total synthesis of a simplified YM-254890 analog
Rensing DT, et al.
Organic Letters, 17(9), 2270-2273 (2015)
Synthesis of Biologically Relevant Compounds by Ruthenium Porphyrin Catalyzed Amination of Benzylic C-H Bonds
Zardi P, et al.
Organometallics, 33(9), 2210-2218 (2014)

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