346861
(S)-(−)-5-Hydroxymethyl-2(5H)-furanone
98%
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About This Item
Empirical Formula (Hill Notation):
C5H6O3
CAS Number:
Molecular Weight:
114.10
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3537455
Assay:
98%
Product Name
(S)-(−)-5-Hydroxymethyl-2(5H)-furanone, 98%
InChI
1S/C5H6O3/c6-3-4-1-2-5(7)8-4/h1-2,4,6H,3H2/t4-/m0/s1
SMILES string
OC[C@H]1OC(=O)C=C1
InChI key
AWNLUIGMHSSXHB-BYPYZUCNSA-N
assay
98%
optical activity
[α]20/D −144°, c = 1 in H2O
mp
41-43 °C (lit.)
functional group
ester
hydroxyl
storage temp.
2-8°C
Quality Level
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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
11 - Combustible Solids
wgk
WGK 3
flash_point_f
235.4 °F - closed cup
flash_point_c
113 °C - closed cup
ppe
Eyeshields, Gloves, type N95 (US)
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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)
Synthesis of 3′-ethynylthymidine, 3′-vinylthymidine and 3′-bromovinylthymidine as potential antiviral agents
Sahlberg C
Tetrahedron Letters, 33(5), 679-682 (1992)
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)
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