397242-80-7

Upstream product

• 14233-64-8 tri-O-benzyl-D-arabinolactone 
• 160549-10-0 2,3,5-tri-O-benzyl-D-arabinofuranose 
• 158349-27-0 (3S,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidin-2-one 
• 137741-24-3 (2S,3R,4R)-4-azido-2,3,5-tribenzyloxy-1-pentanal 
• 397242-79-4 1-((2R,3R,4S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-hydroxy-pyrrolidin-1-yl)-2,2,2-trifluoro-ethanone 
• 537030-19-6 (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide 

Downstream Products

• 397242-82-9 ((2S,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-ylmethyl)-phosphonic acid dimethyl ester 
• 108692-47-3 (2R,3R,4R)-2-hydroxymethyl-3,4-dihydro-2H-pyrrole-3,4-diol 
• 1047990-82-8 2,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-(pent-4-enoylamido)-N-(1,1,3,3-tetramethylbutyl)-D-manno-hexonamide 
• 1047990-81-7 2,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-(pent-4-enoylamido)-N-(1,1,3,3-tetramethylbutyl)-D-gluco-hexonamide 
• 909870-26-4 (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-tertbutylpyrrolidine-2-carboxamide 
• 1437657-37-8 (2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-cyclohexylpyrrolidine-2-carboxamide 
• 909870-24-2 C₃₆H₄₄N₂O₅ 
• 909870-25-3 C₃₆H₄₄N₂O₅ 
• 909870-51-5 C₃₈H₄₆N₂O₅ 
• 909870-52-6 C₃₈H₄₆N₂O₅ 
• 147060-64-8 (2R,3R,4R,5R)-3,4-dihydroxy-2-(hydroxymethyl)-5-methylpyrrolidine 
• 188744-98-1 (2R,3R,4R,5R)-4-(hydroxy)-2-(hydroxymethyl)-5-(4-hydroxyphenyl)pyrrolidin-3-ol 
• 1570184-05-2 (2S,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidine 
• 1105054-51-0 (2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolidine-2-carbonitrile 

Relevant academic research and scientific papers

Concise synthesis of bicyclic iminosugarsviareductive functionalization of sugar-derived lactams and subsequent RCM reaction

An efficient method for the synthesis of bicyclic iminosugars has been developed. The strategy is based on the partial reduction of sugar-derived lactams by Schwartz's reagent and tandem stereoselective nucleophile addition dictated by Woerpel's model which affords polyhydroxylated cyclic amines as key intermediates. Introduction of a vinyl or allyl group to the iminosugar produces diene derivatives that can be subjected to the ring-closing metathesis reaction (RCM) to furnish polyhydroxylated pyrrolizidine, indolizidine and quinozilidine derivatives in good to excellent yields. This sequence of reactions has been applied to the formal synthesis of hyacinthacine A2, a polyhydroxylated pyrrolizidine alkaloid.

Synthesis of polyhydroxylated piperidine and pyrrolidine peptidomimetics via one-pot sequential lactam reduction/Joullié-Ugi reaction

A direct approach to the synthesis of polyhydroxylated piperidine and pyrrolidine peptidomimetics is described. The presented strategy is based on one-pot reduction of sugar-derived lactams with Schwartzs reagent followed by a multicomponent Ugi-Joullié reaction.

Sugar-derived cyclic imines: One-pot synthesis and direct functionalization

A simple method for the synthesis of sugar-derived imines by a Schwartz's reagent reduction of easily available sugar lactams has been described. A direct addition of nucleophiles to the generated in situ cyclic imines and subsequent deprotection of hydroxyl function allows to convert sugar lactams in polyhydroxylated pyrrolidines and piperidines.

Synthesis of polyhydroxylated quinolizidine and indolizidine scaffolds from sugar-derived lactams via a one-pot reduction/Mannich/Michael sequence

A direct approach to the synthesis of indolizidine and quinolizidine scaffolds of iminosugars is described. The presented strategy is based on a one-pot sugar lactam reduction with Schwartz's reagent followed by a diastereoselective Mannich/Michael tandem reaction of the resulting sugar imine with Danishefsky's diene. The stereochemical course of the investigated reaction has been explained in detail. The obtained bicyclic products are attractive building blocks for the synthesis of various naturally occurring polyhydroxylated alkaloids and their derivatives.

Chiral pyrroline-based Ugi-three-component reactions are under kinetic control

Although it is often assumed that the stereochemistry in Ugi multicomponent reactions is determined in the final Mumm rearrangement step, experimental and computational evidence that Ugi reactions on hydroxylated pyrrolines proceed under kinetic control is reported. The stereochemistry of the reaction is established with the addition of the isocyanide to the intermediate iminium ion, whose conformation is determined by its substitution pattern.

Mechanistic investigations of the phosphine-mediated nitrone deoxygenation reaction and its application in cyclic imine synthesis

Carbohydrate-derived cyclic nitrones were deoxygenated to form the corresponding imines using tributylphosphine. Experimental and theoretical investigations by the way of MP2 calculations suggest a revision of the mechanism initially proposed by Kurtzweil

Nucleophilic additions to cyclic nitrones en route to iminocyclitols - Total syntheses of DMDP, 6-deoxy-DMDP, DAB-1, CYB-3, nectrisine, and radicamine B

Highly diastereoselective nucleophilic additions to cyclic nitrones derived from L-malic acid and D-arabinose have been used for the construction of enantiomerically pure polyhydroxylated pyrrolidines. The synthetic strategy adopted was based on an oxidat

A new concise synthesis of nectrisine and its facile conversion to phosphonoazasugars

The synthesis of new sugar-derived phosphonic acids from protected nectrisine is described. The key step is a highly stereoselective addition of a phosphonate anion to a sugar-derived dihydropyrrole to provide a versatile synthetic intermediate which can be functionalised in multiple ways.