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446041

Sigma-Aldrich

(1S,4R)-cis-4-Acetoxy-2-cyclopenten-1-ol

≥99%

Synonym(s):

(1R,3S)-(+)-cis-4-Cyclopentene-1,3-diol 1-acetate, (1R,3S)-4-Cyclopentene-1,3-diol 1-acetate, (1R,4S)-cis-4-Hydroxy-2-cyclopentenyl acetate

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About This Item

Empirical Formula (Hill Notation):
C7H10O3
CAS Number:
60410-16-4
Molecular Weight:
142.15
Beilstein:
4663992
MDL number:
MFCD00078933
UNSPSC Code:
12352108
PubChem Substance ID:
24868219
NACRES:
NA.22

Quality Level

100

Assay

≥99%

form

solid

optical activity

[α]20/D +68°, c = 2.3 in chloroform

mp

49-51 °C (lit.)

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+/m1/s1

InChI key

IJDYOKVVRXZCFD-RQJHMYQMSA-N

Application

(1S,4R)-cis-4-Acetoxy-2-cyclopenten-1-ol can be used as:
  • A building block for the synthesis of biologically significant carbocyclic nucleosides and prostaglandins.
  • A starting material in the synthesis of azasugar analogs.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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
BCCF2596
BCBZ7941
BCBW9306
BCBW3611
BCBM3239V

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Theil, F. et al.
Journal of the Chemical Society. Perkin Transactions 1, 255-255 (1996)
An improved preparation of highly enantiomerically enriched (R)-(+)-4-tert-butyldimethylsiloxy-2-cyclopenten-1-one
Myers AG, et al.
Tetrahedron Letters, 37(18), 3083-3086 (1996)
(4R)-(+)-tert-Butyldimethylsiloxy-2-Cyclopenten-1-one: 2-Cyclopenten-1-one, 4-[[(1, 1-dimethylethyl) dimethylsilyl] oxy]-,(R)-
Paquette LA,
Organic Syntheses, 73(18), 36-36 (1996)
Synthesis of base-modified noraristeromycin derivatives and their inhibitory activity against human and Plasmodium falciparum recombinant S-adenosyl-L-homocysteine hydrolase
Kitade Y, et al.
Tetrahedron, 58(7), 1271-1277 (2002)
Myers, A.G. et al.
Tetrahedron Letters, 37, 3083-3083 (1996)
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