348902

(S)-γ-Hydroxymethyl-γ-butyrolacton

95%

• Synonym(e): (S)-(+)-Dihydro-5-(hydroxymethyl)-2(3H)-furanon, (S)-4,5-Dihydro-5-hydroxymethyl-2(3H)-furanon, (S)-5-Hydroxymethyl-2-oxo-tetrahydrofuran
• Empirische Formel (Hill-System): C₅H₈O₃
• CAS-Nummer: 32780-06-6
• Molekulargewicht: 116.12
• Beilstein: 1680284
• MDL-Nummer: MFCD00066224
• UNSPSC-Code: 12352005
• PubChem Substanz-ID: 24861633
• NACRES: NA.22

Eigenschaften

• Assay: 95%
• Form: liquid
• Optische Aktivität: [α]20/D +56°, c = 3 in chloroform
• Optische Reinheit: ee: 98% (GLC)
• Brechungsindex: n20/D 1.471 (lit.)
• bp: 110-115 °C/0.2 mmHg (lit.)
• Dichte: 1.237 g/mL at 25 °C (lit.)
• Lagertemp.: 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
• InChIKey: NSISJFFVIMQBRN-BYPYZUCNSA-N

Beschreibung

Allgemeine Beschreibung

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.[1]

Anwendung

(S)-(+)-Dihydro-5-(hydroxymethyl)-2(3H)-furanone can be used as a chiral synthon to synthesize:

• Potent nucleoside, acetylcholine, and (+)-muricatacin analogs.[2][3][4]
• Mevinic acids, which are LDL cholesterol-lowering agents.[3][5]
• Adenine based anti-HIV agent named β-F-ddA.[6]

Sicherheitshinweise

• Lagerklassenschlüssel: 10 - Combustible liquids
• WGK: WGK 3
• Flammpunkt (°F): 235.4 °F - closed cup
• Flammpunkt (°C): 113 °C - closed cup
• Persönliche Schutzausrüstung: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)