366815-76-1

Basic information

• Product Name: (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)piperidine
• Synonyms: (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)piperidine
• CAS NO: 366815-76-1
• Molecular Weight: 417.548
• Mol File: 366815-76-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)piperidine(366815-76-1)
• EPA Substance Registry System: (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)piperidine(366815-76-1)

Safety Data

• Hazardous Substances Data: 366815-76-1(Hazardous Substances Data)

Upstream product

• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 160549-11-1 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose 
• 366815-67-0 3,4-bis-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyridine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester 
• 366815-75-0 (2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-hydroxy-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester 
• 366815-73-8 ((1R,2R,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-hex-5-enyl)-carbamic acid 9H-fluoren-9-ylmethyl ester 

Downstream Products

• 53185-12-9 D-fagomine 

Relevant articles and documents

Concise and highly stereoselective syntheses of D-fagomine and 2-epi-fagomine

Highly stereoselective total syntheses of polyhydroxylated piperidines D-fagomine and 2-epi-fagomine have been developed starting from 3,4,6-tri-O-benzyl-D-glucal which is a derivative of D-Glucose. Key steps in the synthesis of these azasugars involved N-Boc-protected amine preparation from oxime followed by stereo specific iodination of alcohol and cascade cyclization triggered by N-Boc deprotection.

Chemistry of imino glycals: Preparation and application to the synthesis of (+)-fagomine

The synthesis of imino glucal 2 from tri-O-benzyl-D-glucal in 8 steps is described. This novel imino sugar building block is further converted into (+)-fagomine by a two-step hydrogenation sequence.