348902
(S)-(+)-Dihydro-5-(hydroxymethyl)-2(3H)-furanone
95%
Synonym(s):
(S)-γ-Hydroxymethyl-γ-butyrolactone, (S)-4,5-Dihydro-5-hydroxymethyl-2(3H)-furanone, (S)-5-Hydroxymethyl-2-oxotetrahydrofuran
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About This Item
Empirical Formula (Hill Notation):
C5H8O3
CAS Number:
Molecular Weight:
116.12
Beilstein:
1680284
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
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Assay
95%
form
liquid
optical activity
[α]20/D +56°, c = 3 in chloroform
optical purity
ee: 98% (GLC)
refractive index
n20/D 1.471 (lit.)
bp
110-115 °C/0.2 mmHg (lit.)
density
1.237 g/mL at 25 °C (lit.)
storage temp.
2-8°C
SMILES string
OC[C@@H]1CCC(=O)O1
InChI
1S/C5H8O3/c6-3-4-1-2-5(7)8-4/h4,6H,1-3H2/t4-/m0/s1
InChI key
NSISJFFVIMQBRN-BYPYZUCNSA-N
General description
Dihydro-5-(hydroxymethyl)-2(3H)-furanone is a chiral building block widely used in the synthesis of many natural products and few biologically significant compounds like anti-HIV dideoxynucleosides. It is also used in the synthesis of optically active ligands.
Application
(S)-(+)-Dihydro-5-(hydroxymethyl)-2(3H)-furanone can be used as a chiral synthon to synthesize:
- Potent nucleoside, acetylcholine, and (+)-muricatacin analogs.
- Mevinic acids, which are LDL cholesterol-lowering agents.
- Adenine based anti-HIV agent named β-F-ddA.
Storage Class Code
10 - Combustible liquids
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
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A concise synthesis of anti-viral agent F-ddA, starting from (S)-dihydro-5-(hydroxymethyl)-2 (3H)-furanone
Choudhury A, et al.
Tetrahedron Letters, 44(2), 247-250 (2003)
Enantio-and diastereoisomers of 2, 4-dimethoxy-5-(2, 3-dideoxy-5-O-tritylribofuranosyl) pyrimidine. 2′, 3′-Dideoxy pyrimidine C-nucleosides by palladium-mediated glycal-aglycon coupling
Zhang HC and Daves Jr GD
The Journal of Organic Chemistry, 58(9), 2557-2560 (1993)
Blackwell, C.M. et al.
The Journal of Organic Chemistry, 57, 5597-5597 (1992)
Stereospecific synthesis of (+)-muricatacin: a biologically active acetogenin derivative
Figadere B, et al.
Tetrahedron Letters, 32(51), 7539-7542 (1991)
Dihydro-5-(hydroxymethyl)-2(3H)-furanone
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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