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270148

Sigma-Aldrich

Methyl (R)-(−)-3-hydroxy-2-methylpropionate

99%

Synonym(s):

(−)-Methyl D-β-hydroxyisobutyrate, (R)-(−)-3-Hydroxy-2-methylpropionic acid methyl ester

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About This Item

Linear Formula:
HOCH2CH(CH3)CO2CH3
CAS Number:
Molecular Weight:
118.13
Beilstein:
3587507
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

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

76-77 °C/12 mmHg (lit.)

density

1.066 g/mL at 25 °C (lit.)

functional group

ester
hydroxyl

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-/m1/s1

InChI key

ATCCIZURPPEVIZ-SCSAIBSYSA-N

Application

Methyl (R)-(-)-3-hydroxy-2-methylpropionate may be used in the preparation of (S)-(4-benzyloxy-3-methylbut-1-ynyl)triethylsilane. It may also be used as a starting material in the total synthesis of (-)-discodermolide, (-)-stemoamide and (-)-stemospironine.
The (R)- and (S)-isomers are bifunctional building blocks for the synthesis of a wide variety of optically active molecules.

Storage Class Code

3 - Flammable 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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

270148-1G:
270148-VAR:
270148-BULK:
270148-5G:
270148-25G:


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Total Synthesis of (-)-Stemospironine.
Williams DR, et al.
Organic Letters, 3(17), 2721-2724 (2001)
Tetrahedron Letters, 34, 5939-5939 (1993)
Distinct binding and cellular properties of synthetic (+)-and (-)-discodermolides.
Hung DT, et al.
Chemistry & Biology, 1(1), 67-71 (1994)
Recent progress in the chemistry of the Stemona alkaloids.
Pilli RA and de Oliveira MDCF.
Natural Product Reports, 17(1), 117-127 (2000)
Journal of the Chemical Society. Perkin Transactions 1, 759-759 (1993)

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