96648-52-1

Upstream product

• 127391-16-6 3-[(2R,3S)-3-((1R,2R)-3-Benzyloxycarbonylamino-1,2-dihydroxy-propyl)-oxiranyl]-propionic acid ethyl ester 
• 98362-03-9 (1S,2R,8R,8aS)-8-hydroxy-1,2-(iso-propylidenedioxy)octahydro-5-indolizidinone 
• 111423-79-1 (1S,2R,8R,8aS)-1,8-di-O-benzyloctahydro-1,2,8-indolizinetriol 
• 228098-81-5 (1S,2R,8R,8aS)-8-hydroxy-1,2-O-iso-propylideneoctahydro-1,2,8-indolizidine triol 
• 111424-00-1 (5R,6S)-5-(benzyloxy)-6-<(1S,2R)-<1-(benzyloxy)-2,3-dihydroxy>propyl>-2-piperidone 
• 1314241-32-1 (3aS,4S,6aR)-tert-butyl 4-((R)-1-hydroxybut-3-enyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate 
• 1314241-33-2 (3aS,4R,6aR)-tert-butyl 4-((R)-1-(tert-butyldimethylsilyloxy)but-3-enyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 
• 1314241-29-6 (3aS,6S,6aS)-tert-butyl 4-acetoxy-6-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 
• 178456-77-4 tert-butyl (3aS,4S,6aR)-4-(hydroxymethyl)-2,2-dimethyltetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 
• 178456-76-3 (2R,3S,4R)-N-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4-dihydroxyproline 
• 178456-75-2 (3aS,4S,6aR)-tert-butyl 4-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 
• 178456-74-1 (3aS,4S,6aS)-tert-butyl 4-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 
• 105878-89-5 (1R,5S,6S,4'S)-7-benzyloxycarbonyl-3,3-dimethyl-6-4'-2',2'-dimethyl-1',3'-dioxanyl-2,4-dioxa-7-azabicyclo<3.3.0>octane 
• 105929-15-5 (1R,5S,6S,1'S)-7-benzyloxycarbonyl-6-1',2'-dihydroxyethyl-3,3-dimethyl-2,4-dioxa-7-azabicyclo<3.3.0>octane 

Relevant academic research and scientific papers

Epimerization of C5 of an: N -hydroxypyrrolidine in the synthesis of swainsonine related iminosugars

Epimerization of C5 of an N-hydroxypyrrolidine ring by regioselective oxidation to a nitrone followed by diastereoselective reduction provides a new approach to the synthesis of swainsonine and related compounds. The only protection in the synthesis of the potent mannosidase inhibitor DIM (1,4-dideoxy-1,4-imino-d-mannitol) was the acetonation of d-mannose.

Intramolecular 5-endo-trig aminopalladation of β-hydroxy-γ- alkenylamine: Efficient route to a pyrrolidine ring and its application for the synthesis of (-)-8,8a-di-epi-swainsonine

The intramolecular aminopalladation reaction of l-serine derived β-hydroxy-γ-alkenylamines undergoes 5-endo-trig cyclization to furnish pyrrolidine rings in high yields. The pyrrolidines thus obtained were used in the synthesis of (-)-8,8a-di-epi-swainsonine, a specific and competitive inhibitor (Ki value 2 × 10-6 M) of lysosomal α-mannosidases.

Synthesis of pyrrolidine iminosugars, (-)-lentiginosine, (-)-swainsonine and their 8a-epimers from d-glycals

Synthesis of pyrrolidine iminosugars has been described from d-glycals via dihydroxylation, oxidative cleavage and double nucleophilic displacement as the key steps. The pyrrolidines obtained have been utilized for the synthesis of important bicyclic iminosugars, viz. (-)-lentiginosine and (-)-swainsonine and their 8a-epimers, which are known to be glycosidase inhibitors.

A flexible enantioselective approach to 3,4-dihydroxyprolinol derivatives by SmI2-mediated reductive coupling of chiral nitrone with ketones/aldehydes

A flexible enantioselective approach to polyhydroxylated prolinol derivatives was described, which is based on the samarium diiodide-mediated reductive coupling of the chiral nitrone (3S,4R)-8, derived from d-isoascorbic acid with aldehydes/ketones. Thereby, polyhydroxyprolinol derivatives 9a-e and 9h-j were obtained from aromatic ketones and aliphatic aldehydes in good to excellent yields of 65-91%. These reductive hydroxyalkylations are highly diastereoselective in establishing the C-4 stereogenic center. By this way, the asymmetric syntheses of (-)-8a-epi-swainsonine (4) and (-)-8,8a-di-epi- swainsonine (5) have been achieved.

A facile synthesis of 1,4-dideoxy-1,4-imino-l-ribitol (LRB) and (-)-8a-epi-swainsonine from d-glutamic acid

A facile synthesis of (-)-8a-epi-swainsonine 2 and 1,4-dideoxy-1,4-imino-l- ribitol (LRB) 4 has been achieved by using the versatile building block 3, which was available from cheap d-glutamic acid. The new forming stereogenic center in synthesis of 2 was constructed by highly selective reduction of the ketone 13 with Li(t-BuO)3AlH in THF (dr=95:5).

De novo asymmetric synthesis of 8a-epi-swainsonine

(Chemical Equation Presented) An enantioselective and diastereocontrolled approach to 8a-epi-D-swainsonine has been developed from achiral furfural. The key step to this synthesis was a one-pot procedure for the hydrogenolytic removal of two protecting groups and two intramolecular reductive amination reactions. The absolute stereochemistry was introduced by asymmetric Noyori reduction of furfuryl ketone. This route relies on diastereoselective palladium-catalyzed glycosylation to install the anomeric bond, and Luche reduction, diastereoselective dihydroxylation to set up the manno- stereochemistry of the indolizidine precursor.

An Acylnitroso Cycloaddition Approach to the Synthesis of Highly Oxygenated Indolizidine Alkaloids

A synthetic approach to the synthesis of highly oxygenated indolizidine alkaloids is described.A key feature of the approach is intramolecular cycloaddition between an acylnitroso dienophile and a tethered diene moiety, followed by ring contraction of the 1,2-oxazine so formed to a pyrrolidine.The requisite intermediates were prepared in optically pure form from L-glutamic acid.