(4R)-2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde

Abstract

[15186-48-8] C6H10O3 (MW 130.14) InChI = 1S/C6H10O3/c1-6(2)8-4-5(3-7)9-6/h3,5H,4H2,1-2H3/t5-/m0/s1 InChIKey = YSGPYVWACGYQDJ-YFKPBYRVSA-N (a fully oxygenated three-carbon chiral electrophile employed for a variety of uses: as a stereochemical probe in nucleophilic additions; as a chiral starting material in total synthesis of sugars and nucleosides, β-lactams, and numerous complex natural products; as a starting material for other chiral building blocks) Alternate Name: (R)-glyceraldehyde acetonide, d-glyceraldehyde acetonide, 2,3-O-isopropylidene-d-glyceraldehyde. Physical Data: bp 72–74 °C/30 mmHg; [α]D + 80.1 (c 1.5, benzene)2 Solubility: freely soluble in organic solvents; forms a readily soluble hydrate in water, readily soluble in alcohols as the corresponding hemiacetal. Analysis of Reagent Purity: analytical methods for determination of enantiomeric purity have been reported.6 Preparative Methods: prepared in two steps from d-mannitol via bis-ketalization to 1,2:5,6-bis-O-(1-methylethylidene)-d-mannitol, followed by oxidative cleavage with Sodium Periodate in dichloromethane.2 Classically obtained from d-mannitol by bis-ketalization and oxidative cleavage with lead tetraacetate.3 Bis-ketalization has been accomplished under a range of conditions;4 a comparative study of the most commonly employed methods has appeared.5 Purification: distilled under reduced pressure immediately prior to use. Partially polymerized material may be cracked by distillation under reduced pressure at 100 °C.2 Handling, Storage, and Precautions: to help prevent polymerization, anhydrous material is best stored dry at refrigerator or freezer temperatures and distilled immediately prior to use. Incompatible with acids, strong bases, and oxidizing and reducing agents.