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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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

00848-100MG:
00848-BULK:
00848-500MG:
00848-VAR:

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Certificates of Analysis (COA)

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

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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)
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)
(+)-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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