849928-64-9

Upstream product

• 1175524-38-5 (5R,6S)-tert-butyl 5-(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 220317-59-9 tert-butyl (R)-4-[(R)-1-hydroxybut-3-enyl]-2,2-dimethyloxazolidine-3-carboxylate 
• 132328-52-0 (4S,1'R)-4-(1'-hydroxybut-3'-enyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 100-39-0 benzyl bromide 
• 102308-32-7 (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 1301261-30-2 C₂₀H₃₉NO₄Si 
• 1301261-29-9 C₂₅H₄₅NO₇SSi 
• 1301261-34-6 C₁₉H₃₁NO₇S 
• 1301261-33-5 C₂₂H₃₅NO₇S 
• 1301261-32-4 C₂₁H₃₃NO₅ 
• 1301261-31-3 tert-butyl (S)-4-((R)-1-(benzyloxy)but-3-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate 
• 448896-88-6 (8R,8aS)-8-hydroxy-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one 
• 849928-63-8 (8R,8aS)-8-benzyloxyhexahydrooxazolo[3,4-a]pyridin-3-one 

Downstream Products

• 1207962-77-3 C₁₈H₂₅NO₅ 
• 72741-87-8 swainsonine 
• 162470-36-2 (-)-8-benzyloxy-swainsonine 
• 849928-69-4 (2S,3R,1'S,2'R)-N-tert-butoxycarbonyl-3-benzyloxy-2-[2'-ethoxycarbonyl-1',2'-dihydroxyethyl]piperidine 
• 849928-71-8 (1S,2R,8R,8aS)-8-benzyloxy-1,2-dihydroxyhexahydroindolizin-3-one 
• 849928-65-0 (2R,3R)-3-Benzyloxy-2-formyl-piperidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis of polyhydroxylated indolizidines and piperidines from Garner's aldehyde: Total synthesis of (-)-swainsonine, (+)-1,2-di-epi-swainsonine, (+)-8,8a-di-epi-castanospermine, pentahydroxy indolizidines, (-)-1-deoxynojirimycin, (-)-1-deoxy-altro-nojirimycin, and related diversity

Diastereoselective and diverse synthesis of polyhydroxylated indolizidines and piperidines have been described, where a common chiral intermediate 2-(hydroxymethyl) piperidine-3-ol is converted into (-)-swainsonine, (+)-1,2-di-epi-swainsonine, (+)-8,8a-di-epi-castanospermine, pentahydroxy indolizidines, (-)-1-deoxynojirimycin, (-)-1-deoxy-altro-nojirimycin, and related diversity. The key steps were hydroxy directed intramolecular aminomercuration, Mitsunobu cyclization, and diastereoselective dihydroxylation.

Stereoselective formal total synthesis of (-)-swainsonine from Garner's aldehyde

A simple and facile stereoselective formal total synthesis of (-)-swainsonine has been reported starting from Garner's l-serine derived oxazolidine aldehyde. Our synthetic strategy involves stereoselective allylation and Still olefination as key intermedi

Facile syntheses of enantiopure 3-hydroxypiperidine derivatives and 3-hydroxypipecolic acids

(Chemical Equation Presentation) Facile syntheses of enantiopure trans- and cis-3-hydroxypiperidine derivatives and 3-hydroxypipecolic acids are reported, featuring Rh-catalyzed cyclohydrocarbonylation through common intermediates. A diaxial conformation in a 2,3-disubstituted N-Boc-piperidinyl structure is revealed by an X-ray crystallographic analysis.

General approach to glycosidase inhibitors. Enantioselective synthesis of deoxymannojirimycin and swainsonine

(Chemical Equation Presented) Deoxymannojirimycin (2) and swainsonine (4) have been synthesized from each enantiomer of the same bicyclic carbarnate precursor 7. The key intermediate was prepared by a simple and efficient three-step synthesis involving RCM of the diene 8, which in turn is easily accessible in any configuration from enantiomerically enriched 2,3-epoxy-4-penten-1-ol 9.