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54957

Sigma-Aldrich

Methyl (R)-3-hydroxybutyrate

puriss., ≥99.0% (sum of enantiomers, GC)

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About This Item

Linear Formula:
CH3CH(OH)CH2CO2CH3
CAS Number:
3976-69-0
Molecular Weight:
118.13
Beilstein/REAXYS Number:
6130687
EC Number:
223-610-0
MDL number:
MFCD00063289
UNSPSC Code:
12352108
PubChem Substance ID:
329758067

grade

puriss.

assay

≥99.0% (sum of enantiomers, GC)

optical activity

[α]20/D −50±2°, c = 1.3% in chloroform stab. with amylenes

optical purity

enantiomeric ratio: ≥98:2 (GC)

refractive index

n20/D 1.421 (lit.)
n20/D 1.422

bp

56-58 °C/11 mmHg (lit.)

density

1.055 g/mL at 20 °C (lit.)

SMILES string

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

InChI

1S/C5H10O3/c1-4(6)3-5(7)8-2/h4,6H,3H2,1-2H3/t4-/m1/s1

InChI key

LDLDJEAVRNAEBW-SCSAIBSYSA-N

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Other Notes

Important optically active compound for the preparation of various bifunctional building blocks [1][2][3][4]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

163.4 °F - closed cup

flash_point_c

73 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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First total synthesis of grahamimycin A.
Y Kobayashi et al.
The Journal of organic chemistry, 65(21), 7221-7224 (2000-10-14)
R M Garbaccio et al.
Organic letters, 2(20), 3127-3129 (2000-09-29)
A concise, stereospecific synthesis of radicicol dimethyl ether is presented. The strategy relies on a convergent three-stage assembly of the 14-membered lactone which has, as a key transformation, a novel ring-forming metathesis reaction utilizing a vinyl epoxide.
A new synthesis of a key intermediate of beta-lactam antibiotics via diastereoselective alkylation of beta-hydroxy ester.
W H Ham et al.
The Journal of organic chemistry, 65(24), 8372-8374 (2000-12-02)
A. Fischli et al.
Modern Synthetic Methods, 2, 269-269 (1980)
Xiao-Hong Chen et al.
PloS one, 9(4), e94543-e94543 (2014-04-18)
A novel carbonyl reductase (AcCR) catalyzing the asymmetric reduction of ketones to enantiopure alcohols with anti-Prelog stereoselectivity was found in Acetobacter sp. CCTCC M209061 and enriched 27.5-fold with an overall yield of 0.4% by purification. The enzyme showed a homotetrameric

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