355138-93-1

Usage

Chemical Properties

Off-White to Tan Low Melting Solid

Upstream product

• 1241959-38-5 tert-butyl (2S,3S,4R,5S)-2-(benzyloxymethyl)-3,4,5-trihydroxypiperidine-1-carboxylate 
• 1241959-36-3 (2S,3S,4R,5S)-tert-butyl 2-((benzyloxy)methyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate 
• 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 

Relevant academic research and scientific papers

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.

Synthesis of eight 1-deoxynojirimycin isomers from a single chiral cyanohydrin

Eight configurational 1-deoxynojirimycin isomers have been synthesized starting from a chiral cyanohydrin as the common precursor. The cyanohydrin chiral pool building block is easily accessible in large quantities by using almond hydroxynitrile lyase as the chiral catalyst in condensing hydrogen cyanide and crotonaldehyde. Our work complements the large body of literature on the synthesis of 1-deoxynojirimycin derivatives with the distinguishing feature that eight stereoisomers of this important class of glycosidase inhibitors can be derived from a common precursor in an efficient manner.

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.

Synthesis of l-altro-1-deoxynojirimycin, d-allo-1-deoxynojirimycin, and d-galacto-1-deoxynojirimycin from a single chiral cyanohydrin

The chemoenzymatic synthesis of three 1-deoxynojirimycin-type iminosugars is reported. Key steps in the synthetic scheme include a Dibal reduction-transimination-sodium borohydride reduction cascade of reactions on an enantiomerically pure cyanohydrin, itself prepared employing almond hydroxynitrile lyase (paHNL) as the common precursor. Ensuing ring-closing metathesis and Upjohn dihydroxylation afford the target compounds.