27098-03-9

Basic information

• Product Name: botryodiplodin
• Synonyms: botryodiplodin;1-(2-Hydroxy-3-methyltetrahydrofuran-4-yl)ethanone;4-Acetyl-2-hydroxy-3-methyltetrahydrofuran;4-Acetyltetrahydro-3-methylfuran-2-ol
• CAS NO: 27098-03-9
• Molecular Formula: C₇H₁₂O₃
• Molecular Weight: 144.19
• Mol File: 27098-03-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 51°C
• Boiling Point: 202.77°C (rough estimate)
• Flash Point: 101.4°C
• Appearance: /
• Density: 1.0789 (rough estimate)
• Refractive Index: 1.4850 (estimate)
• PKA: 12.79±0.60(Predicted)
• CAS DataBase Reference: botryodiplodin(CAS DataBase Reference)
• NIST Chemistry Reference: botryodiplodin(27098-03-9)
• EPA Substance Registry System: botryodiplodin(27098-03-9)

Safety Data

• Hazardous Substances Data: 27098-03-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H12O3/c1-4-6(5(2)8)3-10-7(4)9/h4,6-7,9H,3H2,1-2H3/t4-,6-,7-/m0/s1

Upstream product

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Relevant articles and documents

Lipase-catalysed deacetylation of botryodiplodin acetate

Enantioselective deacetylation of α-(±)-botryodiplodin acetate was successfully accomplished by means of lipase PS to afford (+)-botryodiplodin and α-(+)-botryodiplodin acetate with high enantiomeric excesses. Enzyme-mediated transesterification of the acetylated molecule with n-butanol, as well as its hydrolysis in several organic solvents, are also reported. The CD spectra of (+)-botryodiplodin and α-(+)-botryodiplodin acetate are also presented.

Organocatalytic Michael addition, a convenient tool in total synthesis. First asymmetric synthesis of (-)-botryodiplodin

The asymmetric Michael addition of propionaldehyde to (2E)-(3-nitro-but-2-enyloxymethyl)-benzene 8, catalyzed by the chiral diamine (S,S)-N-iPr-2,2′-bipyrrolidine, afforded, with 93% ee, a precursor 9 of (-)-botryodiplodin. The nitro functionality of 9 was converted to a ketone via a Nef reaction to give, after a few steps, the enantiomerically enriched (-)-botryodiplodin.

Diastereoselective radical cyclization of bromoacetals: Efficient synthesis of (±)-botryodiplodin

A stereoselective synthesis of (±)-botryodiplodin is presented. The key reaction is a radical cyclization of a bromoacetal (Ueno-Stork reaction). The stereogenic acetal center has been used to control the stereoselectivity of the process: the difficulty in controlling the stereochemistry at C(3) of the tetrahydrofuran moiety during the cyclization step has been overcome by a double one-pot reduction procedure starting from a gem-dibromide.