1184705-55-2

Upstream product

• 824-94-2 p-methoxybenzyl chloride 
• 105-13-5 4-Methoxybenzyl alcohol 
• 214068-24-3 methyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-D-glucopyranoside 
• 214068-17-4 methyl 2-O-(p-methoxybenzyl)-6-O-trityl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 18311-26-7 methyl 6-O-trityl-α-D-glucopyranoside 

Downstream Products

• 1184705-58-5 (3R,4S,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)nona-1,8-diene 
• 1184705-61-0 (3R,4S,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-(p-methoxybenzyloxy)cycloheptene 
• 1184705-64-3 (3R,4R,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-hydroxycycloheptene 
• 1184705-66-5 (3R,4S,5S,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)-5-[(methylsulfanyl)thiocarbonyloxy]cycloheptene 
• 1184705-68-7 (3R,4R,6R)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptene 
• 1184705-74-5 (3R,4R,6S)-6-[(benzyl)(benzyloxycarbonyl)amino]-3,4-bis(benzyloxy)cycloheptanone 
• 1184705-70-1 (2S,3R,5R)-5-[(benzyl)(benzyloxycarbonyl)amino]-2,3-bis(benzyloxy)cycloheptanone 

Relevant academic research and scientific papers

Synthesis of calystegine A3 from glucose by the use of ring-closing metathesis

A synthesis of the nortropane alkaloid calystegine A3 is described from D-glucose. The key step employs a zinc-mediated tandem reaction where a benzyl-protected methyl 6iodo glucoside is fragmented to give an unsaturated aldehyde, which is then transformed into the corresponding benzylimine and allylated in the same pot. The functionalized nona-l,8-diene, thus obtained, is converted into the sevenmembered carbon skeleton in calystegine A3 by ring-closing olefin metathesis. Subsequent deoxygenation by the BartonMcCombie protocol, hydroboration and oxidative workup followed by hydrogenolysis affords calystegine A3. The synthesis uses a total of 13 steps from glucose and confirms the absolute configuration of the natural product.