126177-99-9

Upstream product

• 59983-39-0 (S)-1-amino-2-(methoxymethyl)pyrrolidine 

Downstream Products

• 863128-51-2 (4S,6S)-4-(benzyloxymethyl)-2,2,4,6-tetramethyl-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 
• 876150-59-3 (4S,5R,6S)-4-Benzyloxymethyl-2,2,4,6-tetramethyl-[1,3]dioxan-5-ol 
• 876150-61-7 (S)-1-(benzyloxy)-2-[(4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]propan-2-ol 
• 876150-63-9 [(4S,5R,6S)-4-(benzyloxymethyl)-2,2,4,6-tetramethyl-1,3-dioxan-5-yloxy](tert-butyl)dimethylsilane 

Relevant academic research and scientific papers

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.

Enantioselective Alkylation of 2,2-Dimethyl-1,3-dioxan-5-one Using the SAMP-/RAMP-Hydrazone Method

The lithiated SAMP-hydrazone (S)-3 is used as a chiral 1,3-dihydroxyacetone-enolate equivalent C in overall enantioselective α-alkylations leading to 4-alkyl-2,2-dimethyl-1,3-dioxan-5-ones (S)-5a-i in good overall chemical yields and of high enantiomeric purity (ee = 88 - >/= 93percent.