254606

(−)-Methyl (S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

96%

• Synonym(s): α,β-Isopropylidene-L-glyceric acid methyl ester, Methyl α,β-isopropylidene-L-glycerate, Methyl 2,3-O-isopropylidene-L-glycerate
• Empirical Formula (Hill Notation): C₇H₁₂O₄
• CAS Number: 60456-21-5
• Molecular Weight: 160.17
• Beilstein: 4292352
• MDL number: MFCD00066526
• UNSPSC Code: 12352005
• PubChem Substance ID: 24855396
• NACRES: NA.22

Properties

• Assay: 96%
• form: liquid
• optical activity: [α]20/D −8.5°, c = 1.5 in acetone
• optical purity: ee: ≥96.0% (GLC)
• refractive index: n20/D 1.425 (lit.)
• bp: 84-86 °C/15 mmHg (lit.)
• density: 1.106 g/mL at 25 °C (lit.)
• SMILES string: COC(=O)[C@@H]1COC(C)(C)O1
• InChI: 1S/C7H12O4/c1-7(2)10-4-5(11-7)6(8)9-3/h5H,4H2,1-3H3/t5-/m0/s1
• InChI key: DOWWCCDWPKGNGX-YFKPBYRVSA-N

Description

Application

(−)-Methyl (S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate can be used:

• As a chiral building block to make the key tetrahydrofuran subunit of (−)-gymnodimine, a marine algal toxin.
• To prepare an enedione by reacting with dimethyl methylphosphonate, BuLi, and phenylglyoxal, which in turn is used to synthesize cyclopentenone derivatives.
• As a starting material for the preparation of (S)-4,5-dihydroxy-2,3-pentanedione (DPD), a precursor for autoinducer (AI)-2 in bacteria.

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): 172.4 °F - closed cup
• Flash Point(C): 78 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves