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270148

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

Name: Methyl (<I>R</I>)-(−)-3-hydroxy-2-methylpropionate
Brand: ALDRICH

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:

72657-23-9

Molecular Weight:

118.13

Beilstein:

3587507

MDL number:

MFCD00063450

UNSPSC Code:

12352108

PubChem Substance ID:

24856357

NACRES:

NA.22

Quality Level

200

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.)

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

Related Categories

Chiral Catalysts & Ligands

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.

WGK

WGK 3

Flash Point(F)

176.0 °F

Flash Point(C)

80 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Journal of the Chemical Society. Perkin Transactions 1, 759-759 (1993)

A convergent synthesis of (S)-?-methyl-2-aryltryptamine based gonadotropin releasing hormone antagonists.

Walsh TF, et al.

Tetrahedron, 57(24), 5233-5241 (2001)

Total Synthesis of (-)-Stemospironine.

Williams DR, et al.

Organic Letters, 3(17), 2721-2724 (2001)

Distinct binding and cellular properties of synthetic (+)-and (-)-discodermolides.

Hung DT, et al.

Chemistry & Biology, 1(1), 67-71 (1994)

Tetrahedron Letters, 34, 5939-5939 (1993)

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