177420-29-0

Basic information

• Product Name: (3R,4R)-tert-butyl 3,4-bis(benzyloxy)-5-methylenepiperidine-1-carboxylate
• Synonyms: (3R,4R)-tert-butyl 3,4-bis(benzyloxy)-5-methylenepiperidine-1-carboxylate
• CAS NO: 177420-29-0
• Molecular Weight: 409.525
• Mol File: 177420-29-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (3R,4R)-tert-butyl 3,4-bis(benzyloxy)-5-methylenepiperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R)-tert-butyl 3,4-bis(benzyloxy)-5-methylenepiperidine-1-carboxylate(177420-29-0)
• EPA Substance Registry System: (3R,4R)-tert-butyl 3,4-bis(benzyloxy)-5-methylenepiperidine-1-carboxylate(177420-29-0)

Safety Data

• Hazardous Substances Data: 177420-29-0(Hazardous Substances Data)

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 204992-87-0 (3R,4S)-3,4-Bis-benzyloxy-5-oxo-piperidine-1-carboxylic acid tert-butyl ester 
• 1369810-86-5 (2R,3R)-2,3-bis(benzyloxy)-4-((tert-butoxycarbonylamino)methyl)pent-4-enyl methanesulfonate 
• 1369810-85-4 tert-butyl (3R,4R)-3,4-bis(benzyloxy)-5-hydroxy-2-methylenepentylcarbamate 

Downstream Products

• 1369810-92-3 (3R,4S,5R)-tert-butyl 4,5-bis(benzyloxy)-3-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate 
• 1369810-93-4 (3S,4S,5R)-tert-butyl 4,5-bis(benzyloxy)-3-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate 
• 169105-89-9 isofagomine 
• 275363-98-9 (3R,4R,5S)-3,4-dihydroxy-5-hydroxymethylpiperidine 

Relevant articles and documents

Aza-Claisen rearrangement of 2-C-hydroxymethyl glycals as a versatile strategy towards synthesis of isofagomine and related biologically important azasugars

Synthesis of isofagomine has been achieved by implementation of aza-Claisen rearrangement of 2-C-hydroxymethyl glycals as a key step. The above rearrangement has also been utilized in the synthesis of biologically important polyhydroxylated piperidine frameworks such as isogalactofagomine, ent-isogalactofagomine and their analogues and some other azasugars as glycosidase inhibitors. The Royal Society of Chemistry 2012.

Synthesis of a potent inhibitor of β-glucuronidase

A new glucuronic acid-type iminosugar in which a nitrogen atom is placed in the anomeric positon was synthesized and was proven to potently inhibit β-glucuronidase, with Ki = 79 nM.