355138-93-1

Basic information

• Product Name: 1-DEOXY-L-ALTRONOJIRIMYCIN, HYDROCHLORIDE
• Synonyms: 1-DEOXY-L-ALTRONOJIRIMYCIN, HYDROCHLORIDE;(2S,3S,4R,5S)-2-HydroxyMethyl-3,4,5-piperidinetriol Hydrochloride
• CAS NO: 355138-93-1
• Molecular Formula: C6H14ClNO4
• Molecular Weight: 199.63
• Product Categories: All Inhibitors;Glycosidase Inhibitors;Inhibitors;Carbohydrates & Derivatives
• Mol File: 355138-93-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Methanol (Slightly), Water (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: 1-DEOXY-L-ALTRONOJIRIMYCIN, HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-DEOXY-L-ALTRONOJIRIMYCIN, HYDROCHLORIDE(355138-93-1)
• EPA Substance Registry System: 1-DEOXY-L-ALTRONOJIRIMYCIN, HYDROCHLORIDE(355138-93-1)

Safety Data

• Hazardous Substances Data: 355138-93-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Tan Low Melting Solid

Upstream product

• 1274699-57-8 (S)-tert-butyl 4-((R,E)-1-(benzyloxy)-4-hydroxybut-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1274699-53-4 (S)-tert-butyl 4-((R)-1-(benzyloxy)-4-hydroxybut-2-yn-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1274699-54-5 C₂₇H₄₃NO₅Si 
• 1274699-68-1 (S)-tert-butyl 4-((1S,2R,3R)-1-(benzyloxy)-4-chloro-2,3-dihydroxybutyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1274699-65-8 (S)-tert-butyl 4-((R,E)-1-(benzyloxy)-4-chlorobut-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1274699-62-5 (3S,4R,5S,6S)-5-(benzyloxy)-6-(hydroxymethyl)piperidine-3,4-diol 
• 1274699-63-6 C₂₀H₂₇NO₇S 
• 1274699-61-4 (S)-tert-butyl 4-((1S,2R,3S)-1-(benzyloxy)-2,3-dihydroxy-4-(tosyloxy)butyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1274699-59-0 (S)-tert-butyl 4-((1S,2R,3S)-1-(benzyloxy)-2,3,4-trihydroxybutyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1241959-36-3 (2S,3S,4R,5S)-tert-butyl 2-((benzyloxy)methyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate 
• 1241959-38-5 tert-butyl (2S,3S,4R,5S)-2-(benzyloxymethyl)-3,4,5-trihydroxypiperidine-1-carboxylate 

Relevant articles and documents

Six-Step Syntheses of (-)-1-Deoxyaltronojirimycin and (+)-1-Deoxymannonojirimycin from N-Z-O-TBDPS- l -serinal

Highly stereoselective six-step syntheses of (-)-1-deoxyaltronojirimycin (altro-DNJ) and (+)-1-deoxymannojirimycin (manno-DNJ) from N-Cbz-O-TBDPS-l-serinal are described. Key transformations involve a two-step preparation of a functionalized dihydropyridin-3-one as a common intermediate followed by Luche reduction and dihydroxylation (for altro-DNJ). The same sequence employing an epoxidation/epoxide opening in place of dihydroxylation furnishes manno-DNJ.

Rapid and practical synthesis of (-)-1-deoxyaltronojirimycin

Herein a practical and scalable route to 1-deoxyaltronojirimycin is presented. The target is achieved in 9 steps and 43% yield featuring only two chromatographic purifications.