328313-34-4

Upstream product

• 501-53-1 benzyl chloroformate 
• 328313-32-2 5,6-dideoxy-5-amino-1,2-O-isopropylidene-α-D-gluco-hepto-1,4-furanose 
• 329361-73-1 (1R,2R,3S,4R)-ethyl 3-O-benzyl-5,6-dideoxy-5-benzylamino-1,2-O-isopropylidene-α-D-glucoheptofurannuronate 
• 328313-30-0 3-O-benzyl-5,6-dideoxy-5-(N-benzyl)amino-1,2-O-isopropylidene-α-D-gluco-hepto-1,4-furanose 

Relevant academic research and scientific papers

Stereocontrolled 1,3-addition reaction of silyl ketene acetal to sugar nitrone: Synthesis of D-gluco-homo-1-deoxynojirimycin and L-ido-homo-1-deoxynojirimycin

The 1,3-addition reaction of silyl ketene acetal 6 to D-glucose derived nitrone 7 followed by reductive cleavage of the N-O bond afforded D-gluco- and L-ido-β-amino ester derivatives of 9a and 9b. The diastereoselectivity in addition reaction was improved

Intermolecular Michael addition of substituted amines to a sugar-derived α,β-unsaturated ester: Synthesis of 1-deoxy-D-gluco- and -L-ido-homonojirimycin, 1-deoxy-castanospermine and 1-deoxy-8a-epi-castanospermine

The synthesis of polyhydroxylated piperidine alkaloids, namely, 1-deoxy-D-gluco-homonojirimycin 3a, 1-deoxy-L-ido-homonojirimycin 3b, and indolizidine alkaloids 1-deoxy-castanospermine 5a and 1-deoxy-8a-epi-castanospermine 5b, has been achieved. The key step involved is the intermolecular Michael addition of benzylamine to α,β-unsaturated ester 1, derived from D-glucose, which afforded diastereomeric mixture of β-amino esters 6a and 6b with D-gluco- and L-ido- configuration at C5, respectively. Attempts were made to increase and/or alter the diastereoselectivity at the newly generated stereocenter. The high stereoselectivity, in favor of L-ido-isomer 6b, was achieved under kinetically controlled conditions by using lithium N-benzyl amide as a Michael donor. The β-amino esters 6a and 6b represent common intermediates to target molecules. Thus, LAH reduction of 6a and 6b, individually, gave β-amino alcohol 7a and 7b. Sequential hydrogenolysis, selective protection of the amino group, followed by hydrolysis of the 1,2-acetonide functionality, and hydrogenation gave 3a and 3b, respectively. On the other hand, the β-amino ester 6a was converted to γ-amino ester 13a by Arndt-Eistert synthesis, which on hydrogenolysis and treatment with sodium acetate gave γ-lactam 14a. The LAH reduction afforded pyrrolidene. The N-protection-hydrolysis-hydrogenation cascade successfully executed, and 1-deoxy-castanospermine 5a was obtained in good yield. The same sequence of reactions was applied to β-amino ester 6b, which afforded 1-deoxy-8a-epi-castanospermine 5b.