444286

(R)-(+)-α-Hydroxy-γ-butyrolactone

95%, optical purity ee: 98% (GLC)

• Synonym(s): (R)-4,5-Dihydro-3-hydroxy-2(3H)-furanone
• Empirical Formula (Hill Notation): C₄H₆O₃
• CAS Number: 56881-90-4
• Molecular Weight: 102.09
• Beilstein: 80588
• MDL number: MFCD00211246
• UNSPSC Code: 12352005
• PubChem Substance ID: 24868111
• NACRES: NA.22

Properties

• Assay: 95%
• form: liquid
• optical activity: [α]23/D +66°, c = 1.15 in chloroform
• optical purity: ee: 98% (GLC)
• refractive index: n20/D 1.467 (lit.)
• bp: 133 °C/10 mmHg (lit.)
• density: 1.309 g/mL at 25 °C (lit.)
• SMILES string: O[C@@H]1CCOC1=O
• InChI: 1S/C4H6O3/c5-3-1-2-7-4(3)6/h3,5H,1-2H2/t3-/m1/s1
• InChI key: FWIBCWKHNZBDLS-GSVOUGTGSA-N

Description

Application

(R)-(+)-α-Hydroxy-γ-butyrolactone can be used as a starting material to synthesize:

• δ-Azaproline by reacting with benzyloxycarbonyl aminophthalimide via Mitsunobu reactions.
• Homochiral (R)-2,4-dihydroxybutyramide seco-pseudonucleoside reagents.
• Botryolide B via esterification and ring-closing metathesis reaction.
• Pregnane derivatives containing γ-butyrolactones as potential glucocorticoid agonists.

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves