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346861

Sigma-Aldrich

(S)-(−)-5-Hydroxymethyl-2(5H)-furanone

98%

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About This Item

Empirical Formula (Hill Notation):
C5H6O3
CAS Number:
78508-96-0
Molecular Weight:
114.10
Beilstein:
3537455
MDL number:
MFCD00075370
UNSPSC Code:
12352005
PubChem Substance ID:
24861447
NACRES:
NA.22

Assay

98%

optical activity

[α]20/D −144°, c = 1 in H2O

mp

41-43 °C (lit.)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C5H6O3/c6-3-4-1-2-5(7)8-4/h1-2,4,6H,3H2/t4-/m0/s1

InChI key

AWNLUIGMHSSXHB-BYPYZUCNSA-N

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Application

(S)-(−)-5-Hydroxymethyl-2(5H)-furanone can be used as a starting material in the preparation of:
  • Partially saturated heterocycles via a diastereoselective ring chain formation.
  • A natural product named (+)-muscarine.
  • 3′-Ethynylthymidine as a possible antiviral agent.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of (+)-muscarine from (S)-(-)-5-hydroxymethyl-2 (5H)-furanone
Kang KH, et al.
Tetrahedron Letters, 41(42), 8137-8140 (2000)
Bohrisch, J. et al.
Tetrahedron Letters, 34, 2749-2749 (1993)
Highly diastereoselective ring chain transformation of butonolides to 5-(a-hydroxyalkyl) pyrazolidin-3-ones
Bohrisch J, et al.
Tetrahedron Letters, 34(17), 2749-2752 (1993)
Synthesis of 3′-ethynylthymidine, 3′-vinylthymidine and 3′-bromovinylthymidine as potential antiviral agents
Sahlberg C
Tetrahedron Letters, 33(5), 679-682 (1992)

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