292074-19-2

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 106929-09-3 (2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 121964-05-4 3,4-di-O-benzyloxy-5,6-O-isopropylidene-D-mannitol 
• 111476-62-1 3,4-di-O-benzyl-1,2:5,6-di-O-isopropylidene-D-mannitol 
• 69-65-8 mannitol 

Downstream Products

• 292074-24-9 (4R,5S,6R)-4,5-dibenzyloxy-7-[N-(tert-butoxycarbonyl)amino]-6-methoxymethyloxy-1-pivaloyloxy-2-heptene 
• 292074-25-0 (4R,5S,6R)-4,5-dibenzyloxy-7-[N-(tert-butoxycarbonyl)amino]-6-methoxymethyloxy-2-hepten-1-ol 
• 292074-23-8 (4R,5S,6R)-7-azido-4,5-dibenzyloxy-6-methoxymethyloxy-1-pivaloyloxy-2-heptene 
• 292074-33-0 (2R,3S,4R)-3,4-dibenzyloxy-2-methoxymethyloxy-7-pivaloyloxy-5-heptenamine 
• 292074-26-1 (2R,3R,4R,5R)-3,4-dibenzyloxy-N-tert-butoxycarbonyl-5-methoxymethyloxy-2-vinylpiperidine 
• 292074-28-3 (2R,3R,4S,5R)-(3,4-dibenzyloxy-N-tert-butoxycarbonyl-5-methoxymethyloxy-2-piperidinyl)methanol 
• 292074-32-9 (2R,3R,4R)-1-azido-3,4-dibenzyloxy-7-pivaloyloxy-5-hepten-2-ol 
• 292074-30-7 (4R,5S,6R)-4,5-dibenzyloxy-6,7-isopropylidenedioxy-1-pivaloyloxy-2-heptene 
• 292074-20-5 (2R,3R,4R)-3,4-dibenzyloxy-7-pivaloyloxy-5-heptene-1,2-diol 
• 292074-22-7 (4R,5S,6R)-6,7-epoxy-4,5-dibenzyloxy-1-pivaloyloxy-2-heptene 
• 292074-29-4 (4R,5S,6R)-4,5-dibenzyloxy-6,7-isopropylidenedioxy-2-hepten-1-ol 

Relevant academic research and scientific papers

Palladium(II)-catalyzed cyclization of urethanes and total synthesis of 1-deoxymannojirimycin.

The palladium(II)-catalyzed cyclization of the urethane 8, which was derived from D-mannitol, gave the cyclic compound 9 with excellent diastereoselectivity. During these transformations, the Pd(II) species are not reduced and thus the catalyst can recycle without its reoxidation. The cycloadduct 9 was converted to 1-deoxymannojirimycin.

Palladium(II)-catalyzed cyclization of urethanes and its application to a total synthesis of 1-deoxynojirimycin

We have employed a palladium(II)-catalyzed cyclization of allylic alcohol as a key reaction to achieve a total synthesis of the azasugar 1-deoxynojirimycin from o-mannitol. This reaction should be useful for the stereoselective construction of natural poly-substituted piperidine derivatives.