348902

(S)-(+)-Dihydro-5-(hydroxymethyl)-2(3H)-furanone

95%

• Sinônimo(s): (S)-γ-Hydroxymethyl-γ-butyrolactone, (S)-4,5-Dihydro-5-hydroxymethyl-2(3H)-furanone, (S)-5-Hydroxymethyl-2-oxotetrahydrofuran
• Fórmula empírica (Notação de Hill): C₅H₈O₃
• Número CAS: 32780-06-6
• Peso molecular: 116.12
• Beilstein: 1680284
• Número MDL: MFCD00066224
• Código UNSPSC: 12352005
• ID de substância PubChem: 24861633
• NACRES: NA.22

Propriedades

• Ensaio: 95%
• Formulário: liquid
• atividade óptica: [α]20/D +56°, c = 3 in chloroform
• pureza óptica: ee: 98% (GLC)
• índice de refração: n20/D 1.471 (lit.)
• p.e.: 110-115 °C/0.2 mmHg (lit.)
• densidade: 1.237 g/mL at 25 °C (lit.)
• temperatura de armazenamento: 2-8°C
• cadeia de caracteres SMILES: 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
• chave InChI: NSISJFFVIMQBRN-BYPYZUCNSA-N

Descrição

Descrição geral

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]

Aplicação

(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]

Informações de segurança

• Código de classe de armazenamento: 10 - Combustible liquids
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): 235.4 °F - closed cup
• Ponto de fulgor (°C): 113 °C - closed cup
• Equipamento de proteção individual: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)