Glyceraldehyde diethyl acetal

Under conditions similar to those under which cyclohexene affords cis-cyclo-hexane-l,2-diol in yield of 30-33%, Evans et obtained DL-glyceraldehyde diethyl acetal from acrolein diethyl acetal in 67% yield. A suspension of the acetal... 

For hydroxylation of unsaturated aldehydes it is preferable to use the corresponding acetals glyceraldehyde diethyl acetal is obtained from acrolein diethyl acetal by means of permanganate in aqueous solution.116... 

Glyceraldehyde diethyl acetal is cleaved to glyceraldehyde in 80% yield when shaken with O.In sulfuric acid for 7 days at 20°.81... 

The syntheses of d- and L-2-amino-2-deoxy-arabinose and of l,4-dideoxy-l,4-imino-D-lyxitol 94 have been achieved via the nitro-aldol condensation (Henry s reaction) of 2-O-benzyl-D-glyceraldehyde (R)-25 and the diethyl acetal of nitroacetaldehyde (Scheme 13.39), which gives a 88 12 mixture of the arahino and nZ 6>-adducts. Their reduction and subsequent protection of the amines thus obtained, and then selective tosylation of the primary alcohol and hydrogenolysis, gives 93, which is subsequently converted into 94 [80]. 

An intriguing stereodivergent approach to both enantiomers of slaframine, devised by Carretero and Gdmez Arrayds, commenced with the reductive amination of (/J)-glyceraldehyde acetonide 50 with the diethyl acetal of 4-aminobutanal (Scheme 7) (48). The secondary amine product 51 was transformed in three steps into a 1 1 diastereomeric mixture of a, 3-un5atuiated y-hydroxysulfones 52,... 

As described here, both enantiomers of 3 can be prepared In three steps from commercially available diethyl D- and L-tartrate in up to 70% over-all yield.2 3 5 Procedures to obtain the benzylidene acetal,11 12 with the ensuing reduction step,11. 2 are based on previous literature reports. Both enantiomers of 3 have been used in highly stereoselective nitroaldol additions.3 13 Imines, nitrones, oximes, and nitrile oxides derived therefrom were recently employed in a variety of additions/cycloadditions.14 15 (-)-2-0-Benzyl-L-glyceraldehyde has further been used... 

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