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
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1680284
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
10 - Combustible liquids
wgk
WGK 3
flash_point_f
235.4 °F - closed cup
flash_point_c
113 °C - closed cup
ppe
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
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Total synthesis of dihydromevinolin and a series of related 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors
Blackwell CM, et al.
The Journal of Organic Chemistry, 57(21), 5596-5606 (1992)
Dihydro-5-(hydroxymethyl)-2(3H)-furanone
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Blackwell, C.M. et al.
The Journal of Organic Chemistry, 57, 5597-5597 (1992)