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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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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)
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
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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