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270121

Sigma-Aldrich

Methyl (S)-(+)-3-hydroxy-2-methylpropionate

97%

Synonym(s):

(+)-Methyl L-β-hydroxyisobutyrate, (S)-(+)-3-Hydroxy-2-methylpropionic acid methyl ester

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About This Item

Linear Formula:
HOCH2CH(CH3)CO2CH3
CAS Number:
80657-57-4
Molecular Weight:
118.13
Beilstein:
1720830
MDL number:
MFCD00064520
UNSPSC Code:
12352108
PubChem Substance ID:
24856356
NACRES:
NA.22

Quality Level

200

Assay

97%

form

liquid

optical activity

[α]19/D +26°, c = 4 in methanol

optical purity

ee: 99% (GLC)

refractive index

n20/D 1.425 (lit.)

bp

74 °C/10 mmHg (lit.)

density

1.071 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/C5H10O3/c1-4(3-6)5(7)8-2/h4,6H,3H2,1-2H3/t4-/m0/s1

InChI key

ATCCIZURPPEVIZ-BYPYZUCNSA-N

Application

Methyl (S)-(+)-3-hydroxy-2-methylpropionate may be used as a starting material in the total synthesis of (+)-discodermolide, a potent antimitotic agent.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

176.0 °F - closed cup

Flash Point(C)

80 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Total synthesis of the antimicrotubule agent (+)-discodermolide using boron-mediated aldol reactions of chiral ketones.
Paterson I, et al.
Angewandte Chemie (International Edition in English), 39(2), 377-380 (2000)

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