325700-10-5

Basic information

• Product Name: (2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester
• Synonyms: (2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester
• CAS NO: 325700-10-5
• Molecular Weight: 421.609
• Mol File: 325700-10-5.mol

Chemical Properties

• CAS DataBase Reference: (2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester(325700-10-5)
• EPA Substance Registry System: (2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester(325700-10-5)

Safety Data

• Hazardous Substances Data: 325700-10-5(Hazardous Substances Data)

Upstream product

• 91174-01-5 sodium [(benzyloxy)carbonyl]chloroamide 
• 325699-99-8 (2R,3R)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 325699-97-6 (2R)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-oxo-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 325699-88-5 (2R)-2-(tert-butyldimethylsilyloxymethyl)-6-hydroxy-3-oxo-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 226254-77-9 (R)-[2-(tert-butyl-dimethyl-silyloxy)-1-furan-2-yl-ethyl]-carbamic acid benzyl ester 
• 621-84-1 O-benzyl carbamate 
• 1578-26-3 1-(2'-furyl)-2-trimethylsilanylethan-1-ol 
• 98-01-1 furfural 
• 1487-18-9 (furan-2-yl)ethylene 

Downstream Products

• 14199-63-4 1-deoxymannojirimycin 
• 325700-14-9 (2R,3R,4S,5S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3,4,5-trihydroxy-piperidine-1-carboxylic acid benzyl ester 
• 325700-28-5 (2R,3S)-6-ethoxy-3-hydroxy-2-hydroxymethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 

Relevant articles and documents

Synthesis of D- and L-Deoxymannojirimycin via an Asymmetric Aminohydroxylation of Vinylfuran

(Equation Presented) The Sharpless catalytic asymmetric aminohydroxylation has been applied to 2-vinylfuran, producing β-hydroxyfurfurylamine 5a with enantioexcess of >86% and 21% yield from furfural. The Cbz and TBS protected amino alcohol 5a was converted into both the D- and L-isomers of deoxymannojirimycin (DMJ) and deoxygulonojirimycin in five to seven steps and 48% and 66% overall yields. The key steps include the use of an aza-Achmatowicz reaction, a diastereoselective Luche reduction, diastereoselective dihydroxylation, and a tandem Cbz deprotection/reductive amination.