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335304

Sigma-Aldrich

(S)-(+)-4-Isopropyl-3-propionyl-2-oxazolidinone

98%

Synonym(s):

(S)-3-Propionyl-4-isopropyl-2-oxazolidinone

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About This Item

Empirical Formula (Hill Notation):
C9H15NO3
CAS Number:
77877-19-1
Molecular Weight:
185.22
Beilstein/REAXYS Number:
3542849
MDL number:
MFCD00043401
UNSPSC Code:
12352005
PubChem Substance ID:
24860302
NACRES:
NA.22

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[1]
  • doliculide[2]

Other Notes

Versatile chiral auxiliary for asymmetric synthesis. For a recent review, see Aldrichimica Acta .[3]

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKAA2193V
MKAA2193
06317HD
15006TY
12309PZ

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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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