604789-37-9

Upstream product

• 115828-77-8 (2R,3S,4S)-3,4-bis(benzyloxy)-2-(4-methoxybenzyl)-pyrrolidine 
• 100449-58-9 (2R,3S,4S)-2-(4-methoxybenzyl)-3,4-O-bis-(methoxymethyl)pyrrolidine 
• 23006-20-4 (3R,4S,5R)-N-Benzyl-3,4-dihydroxy-5-p-anisyl-pyrrolidon-2 
• 228396-56-3 {(1R)-1-(N-tert-butoxycarbonylamino)-1-deoxy-1-(p-methoxybenzyl)-2,3-O-isopropylidene-4-chloro-L-threitol} 
• 165877-97-4 (2R,3S,4S)-N-benzyl-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine 
• 478623-17-5 ethyl (2E,4R)-4-(tert-butoxycarbonyl)amino-5-(4-methoxyphenyl)pent-2-enoate 
• 115828-68-7 (2R,3R,4R,5R)-3,4-Bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-carbaldehyde 
• 853092-40-7 (3S,4R)-4-(N-9-phenylfluoren-9-yl)amino-3-acetoxy-5-(p-methoxyphenyl)-1-pentene 
• 1292309-34-2 C₂₄H₃₁NO₈S 
• 1292309-27-3 (R)-2-((4R,5R)-5-((benzyloxycarbonylamino)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methylbenzenesulfonate 
• 1292309-29-5 benzyl ((4R,5S)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolan-4-ylmethyl)carbamate 
• 1292309-31-9 benzyl ((4R,5R)-5-((R)-1-hydroxy-2-(4-methoxyphenyl)ethyl)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl)carbamate 
• 19139-74-3 2,3:4,5-di-O-isopropylidene-D-arabinitol 
• 24150-14-9 benzyl (2R,3R,4R)-3,4-dihydroxy-2-(4-methoxybenzyl)-pyrrolidine-1-carboxylate 

Relevant academic research and scientific papers

Total Synthesis of (-)-Anisomycin

Antibiotic (-)-anisomycin was synthesized starting from D-tyrosine using the addition of electrogenerated dichloro-(methoxycarbonyl)methyl anion to aldehyde 2 as a key reaction.

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.

Practical synthesis of trans-dihydroxybutyrolactols as chiral C4 building blocks and their application to the synthesis of polyhydroxylated alkaloids

Practical syntheses of trans-dihydroxybutyrolactols 2a, 2b and 2c from inexpensive chiral pool compounds l-ascorbic, d- and l-tartaric acid have been achieved on a multigram-scale. The synthetic applications of these chiral building blocks have been demonstrated in the efficient total or formal synthesis of polyhydroxylated alkaloids (+)-lentiginosine and (-)-deacetylanisomycin in concise routes. The Royal Society of Chemistry 2013.

A facile and stereoselective synthesis of the C-2 epimer of (+)-deacetylanisomycin

A short, simple and efficient synthesis of the C-2 epimer of (+)-deacetylanisomycin starting from d-mannitol, utilizing an epoxide opening with a Grignard reagent and acid catalysed unusual intramolecular 5-endo-tet cyclization as key steps has been repor

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.

Stereodivergent syntheses of anisomycin derivatives from D-tyrosine

Enantiomerically pure 2-alkyl-3-acetoxy-4-iodopyrrolidines with all groups cis, and all adjacent groups trans (10 and 17), important precursors for the synthesis of pyrrolidinediols, have been prepared from D-tyrosine through regio- and diastereoselective

Stereoselective synthesis of (-)-deacetylanisomycin

A stereoselective synthesis of (-)-deacetylanisomycin has been achieved from a nitrone derived from 1-threose in 6 steps and 53.7% overall yield, The key step of the synthesis is the nucleophilic addition of a Grignard derivative with complete diastereofacial selectivity. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

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

An efficient synthesis of (-)-deacetylanisomycin starting from D-tyrosine1

The antibiotic (-)-deacetylanisomycin was synthesized starting from D-tyrosine using Sharpless asymmetric dihydroxylation as a key reaction.

Stereoselective synthesis of (-)-deacetylanisomycin

A concise synthesis of (-)-deacetylanisomycin has been achieved via the stereocontrolled reductive alkylation of a protected trihydroxynitrile derived from tartaric acid. The resulting aminotriol was selectively O-mesylated on the primary hydroxyl group a