19713-95-2

Upstream product

• 869660-97-9 (2R,3R,4S)-4-azido-1-O-benzyl-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentane-1,2,3-triol 
• 1963-42-4 2-(p-methoxybenzyl)pyrrole 
• 22862-67-5 2-[(4-methoxyphenyl)methyl]-2,5-dihydro-(1H)-pyrrole 
• 24064-16-2 benzyl 2-[(4-methoxyphenyl)methyl]-2,5-dihydropyrrole-1-carboxylate 
• 824-94-2 p-methoxybenzyl chloride 
• 38769-92-5 4-methoxybenzylmagnesium chloride 
• 82892-41-9 N-((benzyloxy)carbonyl)-4β-hydroxy-3α-iodo-2β-(p-methoxybenzyl)pyrrolidine 
• 34869-05-1 N-((benzyloxy)carbonyl)-2β-(p-methoxybenzyl)-3,4β-oxidopyrrolidine 
• 82916-85-6 2β-(p-methoxybenzyl)-3,4β-oxidopyrrolidine 
• 346588-20-3 1-O-benzyl-2,3-O-(1-methylethylidene)-D-arabinitol 
• 3969-59-3 mannitol triacetonide 
• 13039-93-5 2,2:4,5-di-O-isopropylidene-D-arabinose 
• 19139-73-2 (4S,4’R,5R)-5-[(benzyloxy)methyl]-2,2,2’,2’-tetramethyl-4,4’-bis[1,3-dioxolane] 
• 19139-74-3 2,3:4,5-di-O-isopropylidene-D-arabinitol 

Downstream Products

• 111765-92-5 (2S,3R,4R)-N-(benzyloxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine 
• 111602-18-7 (2S,3R,4R)-3-Acetoxy-2-(4-methoxy-benzyl)-4-(2,2,2-trichloro-ethoxycarbonyloxy)-pyrrolidine-1-carboxylic acid benzyl ester 
• 21497-40-5 (+/-)-anisomycin 
• 82916-86-7 N-((benzyloxy)carbonyl)-3β,4α-dihydroxy-2β-(p-methoxybenzyl)pyrrolidine 

Relevant academic research and scientific papers

A common strategy towards the synthesis of 1,4-dideoxy-1,4-imino-L-xylitol, deacetyl (+)-anisomycin and amino-substituted piperidine iminosugars

A strategy towards the synthesis of three different target molecules, namely 1,4-dideoxy-1,4-imino-L-xylitol, deacetyl (+)-anisomycin and amino-substituted piperidine iminosugars, molecules of potential biological and medicinal significance, is reported from a common amino-vicinal diol intermediate derived from tri-O-benzyl-D-glucal. Construction of the key pyrrolidine ring present in 1,4-dideoxy-1,4-imino-L-xylitol and (+)-anisomycin was a consequence of thermodynamically driven concomitant intramolecular nucleophilic addition reaction of the amino group to the resultant aldehyde obtained by oxidative cleavage of the amino-vicinal diol. Alternatively, double nucleophilic substitution on an amino-diol, after mesylation, with various amines delivered amino-substituted piperidine iminosugars in good yields.

A new approach to (+)-anisomycin

An efficient approach to enantiomerically pure (+)-deacetylanisomycin 2a and a formal synthesis of (+)-anisomycin 2 (11% overall yield in 10 steps) have been achieved through simple and good yielding reactions, starting from 1,2:3,4:5,6-tri-O-isopropylidene-D-mannitol 3. Grignard reaction and intramolecular cyclisation reactions are key steps in the strategy.

Highly diastereoselective additions to polyhydroxylated pyrrolidine cyclic imines: Ready elaboration of aza-sugar scaffolds to create diverse carbohydrate-processing enzyme probes

Representative diastereomeric, erythritol and threitol polyhydroxylated pyrrolidine imine scaffolds have been rapidly elaborated to diversely functionalized aza-sugars through highly diastereoselective organometallic (RM) additions (R = Me, Et, allyl, hex