1430588-26-3

Basic information

• Product Name: (2S,3R,4R)-benzyl 3,4-bis(benzyloxy)-2-(chloromethyl)piperidine-1-carboxylate
• Synonyms: (2S,3R,4R)-benzyl 3,4-bis(benzyloxy)-2-(chloromethyl)piperidine-1-carboxylate
• CAS NO: 1430588-26-3
• Molecular Weight: 480.003
• Mol File: 1430588-26-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3R,4R)-benzyl 3,4-bis(benzyloxy)-2-(chloromethyl)piperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4R)-benzyl 3,4-bis(benzyloxy)-2-(chloromethyl)piperidine-1-carboxylate(1430588-26-3)
• EPA Substance Registry System: (2S,3R,4R)-benzyl 3,4-bis(benzyloxy)-2-(chloromethyl)piperidine-1-carboxylate(1430588-26-3)

Safety Data

• Hazardous Substances Data: 1430588-26-3(Hazardous Substances Data)

Upstream product

• 1430587-89-5 (2R,3R,4R)-benzyl 3,4-bis(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate 

Relevant articles and documents

Total synthesis of d-fagomine and 6-deoxyfagomine

Total synthesis of d-fagomine and 6-deoxyfagomine from readily available d-lyxose is described. The key steps included regioselective and diastereoselective amination, hydroboration-oxidation, and Appel reaction. The reaction of 3,4-anti-tribenzyl ether with chlorosulfonyl isocyanate in toluene at 0 °C afforded 3,4-anti-amino alcohol, an essential compound for the preparation of d-fagomine and 6-deoxyfagomine, with a high diastereoselectivity (dr=26:1) in 74% yield. The origin of diastereoselectivity can be explained by the neighboring group effect, which leads to retention of the stereochemistry.