863128-51-2

Upstream product

• 139153-17-6 ((S)-2-Methoxymethyl-pyrrolidin-1-yl)-((4S,6S)-2,2,4,6-tetramethyl-[1,3]dioxan-5-ylidene)-amine 
• 3587-60-8 Benzyloxymethyl chloride 
• 126177-99-9 ((S)-2-Methoxymethyl-pyrrolidin-1-yl)-[(R)-2,2,4-trimethyl-[1,3]dioxan-(5E)-ylidene]-amine 
• 126178-07-2 (S)-(+)-1-(2,2-dimethyl-1,3-dioxan-5-ylidenamino)-2-methoxymethylpyrrolidine 
• 74181-34-3 2,2,-dimethyl-1,3-dioxan-5-one 
• 863128-50-1 [(4R,5E,6S)-4-(benzyloxymethyl)-2,3,4,6-tetramethyl-1,3-dioxan-5-ylidene][(S)-2-(methoxymethyl)pyrrolidin-1-yl]amine 

Downstream Products

• 876150-59-3 (4S,5R,6S)-4-Benzyloxymethyl-2,2,4,6-tetramethyl-[1,3]dioxan-5-ol 
• 876150-63-9 [(4S,5R,6S)-4-(benzyloxymethyl)-2,2,4,6-tetramethyl-1,3-dioxan-5-yloxy](tert-butyl)dimethylsilane 
• 876150-61-7 (S)-1-(benzyloxy)-2-[(4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]propan-2-ol 

Relevant academic research and scientific papers

First asymmetric synthesis of (+)-sordidin and (-)-7-epi-sordidin, aggregation pheromones of the banana weevil cosmopolites sordidus

The asymmetric synthesis of (1S,3R,5R,7S)-(+)-sordidin and 7-epi-(1S,3R,5R,7R)-(-)-sordidin, both components of the natural male-produced aggregation pheromone of the banana weevil Cosmopolites sordidus (Germar), starting from 2,2-dimethyl-1,3-dioxan-5-one is described. Two of the stereogenic centers were generated by three α-alkylations of the corresponding RAMP-hydrazone. Diastereoselective epoxide opening as another key step of the synthesis employing the aza-enolate of 3-pentanone SAEP-hydrazone as nucleophile and subsequent acidic intramolecular acetalisation furnished the sordidin C-7 epimers in good overall yield (39%) as a 1.5:1 diastereomeric mixture. The epimers could be separated by preparative GC and thus, each of them could be obtained in high diastereomeric and enantiomeric purity (de ≥ 97%, ee ≥ 98%).

Asymmetric synthesis of 4′-epi-trachycladines A and B

The first asymmetric synthesis of 4′-epi-trachycladines A and B is reported. Starting from 2,2-dimethyl-1,3-dioxan-5-one the title nucleosides were synthesised in 14 steps employing the SAMP-/RAMP-hydrazone methodology. The dioxanone-SAMP-hydrazone was first transformed into a trisubstituted derivative by a triple α-/α′-alkylation. Removal of the chiral auxiliary and subsequent reduction gave the corresponding alcohol, which could be transformed over four steps into TBS-protected 2′-C-methyl-5′-deoxy- L-lyxose. The trachycladines were then obtained via the corresponding triacetate using standard Vorbrueggen and silyl-Hilbert-Johnson conditions in an overall yield of 18-21%. Such 2′-C-branched ribonucleosides are potential agonists for adenosine receptors and play an important role in drug discovery. Georg Thieme Verlag Stuttgart.