Tartaric dialdehyde

Scheme 2.2.5.15 Highly diastereoselective formation of a bicyclic decadiulose from racemic tartaric dialdehyde by bidirectional chain extension.

Scheme 5.15. Divergent pathways for tandem aldol additions of dihydroxyacetone phosphate (DHAP) with racemic tartaric dialdehyde, catalyzed by fmctose 1,6-bisphosphate (FruA). P = P032 Pase = phosphatase.

The smallest member of such homologous series are the 2,3-dihydroxy succinic (tartaric) dialdehydes. Three stereoisomeric forms are possible, i. e. one meso (erythro) and two enantiomeric (d- and L-threo) compounds (i. e. 3). Because of the enantiotopic nature of the termini of a meso chain, any twofold aldol addition under reagent control imposed by the same chiral biocatalyst would eliminate the element of cj-symmetry and thus effect a terminus differentiation (cf. Scheme 4). For the same reason, enzymes that cannot easily differentiate the two enantiotopic aldehyde groups would lead to the formation of two different. 

Tartaraldehyde, nitromethane, 740 D-Tartaric add, 351, 492,838,909 DL-Tartaric acid, 760 mew-Tartaiic add, 760 meso-Tartaric dialdehyde, 634-635 Teflon, 14, 25 Teflon-Haion, 62,63 Tellurium dibromide, 348 Terephthalic add, 666, 733,1084-1085 o-Terphenyl, 780, 781 p-Terphenyl, 337,931,932,1238 o-Terphenylenemercury, 267 cifrl,8-Tetpin, 950 Terpinolene, 568 Terramycin, 1183... 

Other work with the lower-carbon sugars and related compounds during the years in Basle included the oxidative cleavage of 3,4-0-isopropylidene-D-mannitol with lead tetraacetate, to produce an acetonated tartaric dialdehyde (with H. Appel), the application of the Strecker synthesis to this dialdehyde and to 2,3-0-isopropylidene-D-glyceraldehyde (with L. Feldman), and studies based on glyoxal hemiacetal and nn-tartronaldehydic acid (with E. Baer and H. Nidecker). 

Racemic tartaric dialdehyde has been obtained by a third route by the neutral permanganate oxidation of fumaric dialdehyde tetramethyl acetal. It was convertible into oKo-teloidinone by Robinson condensation and the ketone on reduction yielded oHo-teloidine and pseudo-oKo-teloidine (129). 

Tartaric dialdehyde. Dihydroxysuccindial-dehyde. Tartraldehyde. Tetrodialdose [34361-91-6]... 

Tartaric add dimethyl ether, D-722 Tartaric add, T-12 Tartaric dialdehyde, D-687 Tartraldehyde, D-687 Tartramide, T-12 Tasmin, G-530 Tavidan, H ... 

There is abundant information to support the contention that the lower-melting monoisopropylidene-mannitol (m. p. 85°) is the 3,4-derivative. For example, its tetrabenzoate is identical with that obtained by acetonation of 1,2,5,6-tetrabenzoyl-mannitol,11498 the structure of which is based on independent evidence.114 The larger fragment resulting from the oxidative scission of the D-enantiomorph of the isopropylidene-man-nitol with lead tetraacetate is 2,3-isopropylidene-D-//treo-dihydroxy-succinic dialdehyde, characterized by its subsequent conversion into D-i/ireo-tartaric acid.126 When methylated and hydrolyzed, the L-enantio-morph of the monoketal affords a tetramethyl-mannitol, which, in turn, yields dimethyl-L-glyceraldehyde with lead tetraacetate.127 Each of these facts is in itself proof that the acetone residue occupies the 3,4-position in the mannitol molecule. 

Similar polyacetal structures were prepared by BASF scientists from general dialdehydes and aliphatic hydroxycarboxylic acids derived from sugars [156, 157], shown in Scheme 15. Alternatively, carboxypolyacetals are available by the addition of polyhydroxy carboxylic acids, tartaric acid, for example, to divinyl ethers [158]. 

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