335304
(S)-(+)-4-Isopropyl-3-propionyl-2-oxazolidinone
98%
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Synonym(s):
(S)-3-Propionyl-4-isopropyl-2-oxazolidinone
Empirical Formula (Hill Notation):
C9H15NO3
CAS Number:
Molecular Weight:
185.22
Beilstein:
3542849
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Assay
98%
form
liquid
optical activity
[α]25/D +93°, c = 8.7 in methylene chloride
refractive index
n20/D 1.464 (lit.)
bp
102-106 °C/0.75 mmHg (lit.)
density
1.094 g/mL at 25 °C (lit.)
SMILES string
CCC(=O)N1[C@H](COC1=O)C(C)C
InChI
1S/C9H15NO3/c1-4-8(11)10-7(6(2)3)5-13-9(10)12/h6-7H,4-5H2,1-3H3/t7-/m1/s1
InChI key
HOWPHXVPNNPSAZ-SSDOTTSWSA-N
Application
(S)-(+)-4-Isopropyl-3-propionyl-2-oxazolidinone can be used as a building block to prepare:
- (25S)-cholestenoic-26-acid, a potent ligand for the hormonal DAF-12 receptor in Caenorhabditis elegans
- doliculide
Other Notes
Versatile chiral auxiliary for asymmetric synthesis. For a recent review, see Aldrichimica Acta .
WGK
WGK 3
Flash Point(F)
closed cup
Flash Point(C)
closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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K Iseki et al.
Chemical & pharmaceutical bulletin, 43(11), 1897-1901 (1995-11-01)
A new fluorinated analog of vitamin D2, 24-epi-26,26,26,27,27,27-hexafluoro- 1 alpha,25-dihydroxyvitamin D2, was efficiently synthesized starting from (R)-4-isopropyl-3-propionyl-2- oxazolidinone with high stereochemical control. In all four physiological test systems, the fluorinate vitamin D2 analog was found to be slightly less active
Stereoselective synthesis of the hormonally active (25 S)-δ7-dafachronic acid,(25 S)-δ4-dafachronic acid,(25 S)-dafachronic acid, and (25 S)-cholestenoic acid.
Martin R, et al.
Organic & Biomolecular Chemistry, 6(23), 4293-4295 (2008)
Enantioselective total synthesis of doliculide, a potent cytotoxic cyclodepsipeptide of marine origin and structure-cytotoxicity relationships of synthetic doliculide congeners
Hiroyuki I, et al.
Tetrahedron, 50(45), 12853-12882 (1994)
Ager, D.J., et al.
Aldrichimica Acta, 30, 3-3 (1997)
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