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
• Empirical Formula (Hill Notation): C₅H₈O₃
• CAS Number: 32780-06-6
• Molecular Weight: 116.12
• Beilstein/REAXYS Number: 1680284
• MDL number: MFCD00066224
• UNSPSC Code: 12352005
• PubChem Substance ID: 24861633
• NACRES: NA.22

Properties

• 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

Description

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.

Safety Information

• Storage Class: 10 - Combustible liquids
• wgk_germany: 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)