182298-44-8

Upstream product

• 4933-77-1 (3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde 
• 321142-37-4 7-O-allyl-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-heptopyranose 
• 100-39-0 benzyl bromide 
• 182298-32-4 (R)-2-[(E)-Pyrrolidin-1-ylimino]-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethanol 
• 321142-58-9 7-O-allyl-6-O-benzyl-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-heptopyranose 
• 182298-43-7 [(R)-2-Benzyloxy-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-eth-(E)-ylidene]-pyrrolidin-1-yl-amine 
• 321142-56-7 7-O-allyl-6-O-benzoyl-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-heptopyranose 

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.

Homologation of protected hexoses with Grignard C1 reagents

Derivatives of three stereoisomeric hexodialdo-1,5-pyranosides were reacted with four Grignard C1 reagents: methoxymethyl-, allyloxymethyl-, benzyloxymethyl, and dimethylphenylsilylmethyl-magnesium chlorides. Two stereoisomeric heptoses were obtained in each case in a good yield. The methyl alloside-derived heptosides were accompanied by C-5 inverted products. The addition of Grignard reagents to aldehydes 5-8 has been discussed in terms of parallel α- or β-chelated and Felkin-Anh transition states. It has been found that the silyl Grignard reagent 12 exhibits a strong preference for the formation of heptose derivatives of L-configuration at C-6. (C) 2000 Elsevier Science Ltd.

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.