182298-39-1

Upstream product

• 100-39-0 benzyl bromide 
• 182298-29-9 (R)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-[(E)-pyrrolidin-1-ylimino]-ethanol 
• 65462-15-9 3-O-benzyl-1,2-O-isopropylidene-β-L-arabino-pentodialdo-1,4-furanose 
• 60144-26-5 formaldehyde N,N-tetramethylenehydrazone 
• 23558-05-6 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose 

Downstream Products

• 115243-95-3 (S)-Benzyloxy-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-acetaldehyde 
• 28713-39-5 3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 

Relevant academic research and scientific papers

Stereoselective nucleophilic formylation and cyanation of α-alkoxy- and α-aminoaldehydes

The spontaneous 1,2-addition of formaldehyde N,N-dialkylhydrazones to carbohydrate-derived α-alkoxyaldehydes takes place under neutral conditions and in the absence of catalysts or promoters to afford the corresponding α-hydroxyhydrazones in good to excellent yields and with highly anti diastereoselectivities. Subsequent transformations of the hydrazono group into aldehydes and nitriles following known procedures provide a new entry into the homologation of carbohydrates and the synthesis of cyanohydrins, respectively. Additionally, reaction of methyleneaminopyrrolidine with N-Boc-protected α-aminoaldehydes from natural amino acids efficiently affords the corresponding adducts under the same conditions. From these adducts, a variety of biologically interesting α-hydroxy-β-aminocarbonyl compounds can be accessed upon manipulation of the hydrazone moiety.

Stereospecific addition of formaldehyde dialkylhydrazones to sugar aldehydes. Synthesis of cyanohydrins and α-hydroxy aldehydes

Formaldehyde dialkylhydrazones smoothly add to sugar aldehydes without any need of promoter or catalyst. α-Hydroxy dialkylhydrazones, which are obtained in good yields and high stereoselectivities, have been successfully transformed in cyanohydrins by treatment with magnesium monoperoxyphtalate (MMPP) and in O-protected α-hydroxy aldehydes by ozonolysis or HCl mediated hydrolysis. No racemization was observed in the cleavage of the dialkylhydrazone group.