1430587-89-5

Basic information

• Product Name: (2R,3R,4R)-benzyl 3,4-bis(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate
• Synonyms: (2R,3R,4R)-benzyl 3,4-bis(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate
• CAS NO: 1430587-89-5
• Molecular Weight: 461.558
• Mol File: 1430587-89-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R)-benzyl 3,4-bis(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R)-benzyl 3,4-bis(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate(1430587-89-5)
• EPA Substance Registry System: (2R,3R,4R)-benzyl 3,4-bis(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate(1430587-89-5)

Safety Data

• Hazardous Substances Data: 1430587-89-5(Hazardous Substances Data)

Downstream Products

• 53185-12-9 D-fagomine 
• 1430588-26-3 (2S,3R,4R)-benzyl 3,4-bis(benzyloxy)-2-(chloromethyl)piperidine-1-carboxylate 
• 1430587-92-0 (2R,3R,4R)-2-benzenesulfonyloxymethyl-3,4-bis-benzyloxy-piperidine-1-carboxylic acid benzyl ester 
• 1430588-23-0 (2R,3R,4R)-3,4-bis-benzyloxy-2-methanesulfonyloxymethyl-piperidine-1-carboxylic acid benzyl ester 

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.