Dimethyl-1,3-dioxolane-4-carboxaldehyde

Christopher R. Schmid Eli Lilly and Company, Indianapolis, Indiana, USA 

Alternate Name (R)-glyceraldehyde acetonide, o-glyceraldehyde acetonide, 2,3-O-isopropylidene-D-glyceraldehyde. 

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.  

Preparative Methods prepared in two steps from o-mannitol via bis-ketalization to l,2 5,6-bis-( -(l-methylethylidene)-D-mannitol, followed by oxidative cleavage with sodium periodate in dichloromethane. Classically obtained from o-mannit-ol by bis-ketalization and oxidative cleavage with lead tetraacetate. Bis-ketalization has been accomplished under a range of conditions a comparative study of the most commonly employed methods has appeared.  

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C6H10O3 2,2-dimethyl-1,3-dioxolane-4-carboxaldehyde 5736-03-8 459.55 40.012 2 7983 C6H11Br 5-bromo-2-methyl-2-pentene 2270-59-9 426.15 43.023 1,2... 

Cyclobutyl-cis-4-trans-5-dimethyl- 1,3-dioxolane, by reaction of erythro-3-methane-sulfonyloxy-2-butyl cyclo-butanecarboxylate with sodium borohydride, 51, 12 hydrolysis to cyclobutane-carboxaldehyde, 51, 13 3,5—CYCLOHEXADIENE—1, 2-DI CARBOXYLIC ACID, 50, 50 A1 a-Cyclohexaneacetaldehyde, 53, 104... 

D-(R)-GLYCER ALDEHYDE ACETONIDE (1,3-Dioxolane-4-carboxaldehyde, 2,2-dimethyl, (R)-)... 

L-(S)-Glyceraldehyde acetonide 1,3-Dioxolane-4-carboxaldehyde, 2,2-dimethyl-, L- (8) 1,3-Dioxolane-4-carboxaldehyde, 2,2-dimethyl-, (S)- (9) (22323-80-4) Sodium (meta)periodate Periodic acid, sodium salt (8,9) (7790-28-5) 5,6-0-lsopropylidene-L-gulono-1,4-lactone L-Gulonic add, 5,6-0-(1-methylethylidene)-, y-lactone (11) (94697-68-4)... 

The reagent s moderate facial preference makes it an ideal choice for illustrating the concept of double asymmetric induction. The chiral lithium (Z)-enolate, which also exhibits a moderate enantiofacial preference in reaction with achiral aldehydes, reacts with the reagent to afford a 61 28 ratio of products (eq 6). This mismatched case of asymmetric induction indicates that the facial preferences of the two compounds are working at crosspurposes. With the reagent s enantiomer, (45)-2 -dimethyl-l,3-dioxolane-4-carboxaldehyde, a greater than 97 3 ratio of products is obtained, indicating matched facial preferences. 

Dimethyl l-(tert-butoxycarbonyl)methylphosphonate reacts analogously with N-iodosuccinim-ide in the presence of NaH in THF at 25°C to give an iodinated carbanion which reacted with (/ )-2,2-dimethyl-l,3-dioxolan-4-carboxaldehyde in a Homer-Wadsworth-Emmons reaction to produce the corresponding iodoalkene in 64% overall yield. ... 

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