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00848

Sigma-Aldrich

(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:
60176-77-4
Molecular Weight:
142.15
Beilstein:
4350633
MDL number:
MFCD00210003
UNSPSC Code:
12352108
PubChem Substance ID:
329747151
NACRES:
NA.22

Quality Level

100

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

SMILES string

CC(=O)O[C@H]1C[C@@H](O)C=C1

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

InChI key

IJDYOKVVRXZCFD-NKWVEPMBSA-N

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
046096/1
045055/1
46096/1
45055/1

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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)
Synthesis of novel spinosyn A analogues by Pd-mediated transformations
Tietze LF, et al.
Chemistry?A European Journal , 13(30), 8543-8563 (2007)
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)
(+)-7-Deaza-5 `-noraristeromycin as an anti-trypanosomal agent
Seley KL, et al.
Journal of Medicinal Chemistry, 40(4), 622-624 (1997)

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