270148
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
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3587507
Assay:
99%
Form:
liquid
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
3 - Flammable liquids
wgk
WGK 3
flash_point_f
176.0 °F - closed cup
flash_point_c
80 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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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)
Distinct binding and cellular properties of synthetic (+)-and (-)-discodermolides.
Hung DT, et al.
Chemistry & Biology, 1(1), 67-71 (1994)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 270148-5G | 04061826141786 |
| 270148-1G | 04061838348302 |