00848
(1R,4S)-cis-4-Acetoxy-2-cyclopenten-1-ol
≥98.0% (sum of enantiomers, GC)
Synonym(s):
(1S,4R)-cis-4-Hydroxy-2-cyclopentenyl acetate
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About This Item
Empirical Formula (Hill Notation):
C7H10O3
CAS Number:
Molecular Weight:
142.15
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
4350633
InChI
1S/C7H10O3/c1-5(8)10-7-3-2-6(9)4-7/h2-3,6-7,9H,4H2,1H3/t6-,7+/m0/s1
SMILES string
CC(=O)O[C@H]1C[C@@H](O)C=C1
InChI key
IJDYOKVVRXZCFD-NKWVEPMBSA-N
assay
≥98.0% (sum of enantiomers, GC)
optical activity
[α]20/D −67±2°, c = 2.3% in chloroform
mp
49-51 °C
functional group
ester, hydroxyl
Quality Level
Related Categories
Application
(1R,4S)-cis-4-Acetoxy-2-cyclopenten-1-ol can be used as a reactant in the total synthesis of Bartlett′s brefeldin intermediate, spinosyn A analogs, (+)-7-deaza-5′-noraristeromycin, (±) strychnine and the Wieland-Gumlich aldehyde.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Synthesis of novel spinosyn A analogues by Pd-mediated transformations
Tietze LF, et al.
Chemistry?A European Journal , 13(30), 8543-8563 (2007)
A new approach to (+)-brefeldin A via a nickel-catalyzed coupling reaction of cyclopentenyl acetate and lithium 2-furylborate
Kobayashi Y, et al.
Tetrahedron Letters, 37(34), 6125-6128 (1996)
(+)-7-Deaza-5 `-noraristeromycin as an anti-trypanosomal agent
Seley KL, et al.
Journal of Medicinal Chemistry, 40(4), 622-624 (1997)
Asymmetric Total Syntheses of (-)-and (+)-Strychnine and the Wieland-Gumlich Aldehyde
Knight SD, et al.
Journal of the American Chemical Society, 117(21), 5776-5788 (1995)
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