110261-69-3

Upstream product

• 110261-62-6 benzyl cis-6-(dimethoxymethyl)-3,6-dihydro-3-methyl-2H-1,2-oxazine-2-carboxylate 
• 88818-16-0 benzyl nitrosoformat 
• 72908-59-9 sorbaldehyde dimethylacetal 

Downstream Products

• 449729-69-5 (+/-) 1,6-dideoxyallonojirimycin 
• 110261-71-7 benzyl c-6-(dimethoxymethyl)-3,4,5,6-tetrahydro-t-4,t-5-dihydroxy-r-3-methyl-2H-1,2-oxazine-2-carboxylate diacetate 

Relevant academic research and scientific papers

6-Deoxy-allo-nojirimycin in the racemic and D-series, 6-deoxy-D,L-talo-nojirimycin, their 1-deoxyderivatives and 6-deoxy-2-D,L-allosamine via hetero-Diels-Alder cycloadditions

Diels-Alder cycloaddition of hexadienal dimethylacetal 3 to achiral acylnitroso-dienophile 5a gave the racemic cyclodducts 7a-c and, to chiral chloronitroso-dienophile 6, enantiomerically pure D-10a as sole adduct. Simple chemical transformations led to 6

Syntheses of Amino-dideoxyallose and Amino-deoxyribose Derivatives Using Acylnitroso Dienophiles

The dimethyl acetals 4 of (E)-2,4-pentadienal and of (E,E)- and (E,Z)-2,4-hexadienals undergo regio- and stereospecific cycloaddition reactions with in-situ-generated acylnitroso dienophiles 5a and 5b, leading thereby to the corresponding dihydrooxazines

TOTAL SYNTHESIS OF (+/-) AMINOALLOSE DERIVATIVES

Acylnitroso derivatives 2, which are obtained by in situ oxidation of the corresponding hydroxamic acids, react with the dimethylacetal of hexa-2,4-dienal 1, leading thereby regio- and stereospecifically to the Diels-Alder adducts 3a-3d.Adduct 3b was