132454-50-3

Upstream product

• 69832-48-0 ((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 132454-53-6 (3R,4S,5S)-4,5-Bis-benzyloxymethyl-3-hydroxy-dihydro-furan-2-one 
• 69827-91-4 3-deoxy-1,2-O-(1-methylethylidene)-3-<(phenylmethoxy)methyl>-5-O-(phenylmethyl)-α-D-ribofuranose 
• 26277-33-8 (R)-1-((3aR,5S,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol 
• 69827-89-0 ((3aR,5S,6R,6aR)-5-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-methanol 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 67-56-1 methanol 
• 132454-54-7 Trifluoro-methanesulfonic acid (3R,4R,5S)-4,5-bis-benzyloxymethyl-2-oxo-tetrahydro-furan-3-yl ester 
• 81722-81-8 1,2:5,6-Di-O-isopropyliden-3-C-<(trimethylsilyl)methyl>-α-D-allofuranose 

Downstream Products

• 132454-51-4 (2S,3R)-2,3-Bis-benzyloxymethyl-4-chloro-oxetane 
• 132454-56-9 (2S,3R,4S)-3,4-Bis-benzyloxymethyl-oxetane-2-carbonyl chloride 
• 103913-16-2 (-)-oxetanocin 
• 120293-59-6 α-Oxetanocin 
• 132454-84-3 (2S,4S)-2,3,4-Tris-benzyloxymethyl-oxetane 
• 132454-58-1 N-[9-((2R,3R,4S)-3,4-Bis-benzyloxymethyl-oxetan-2-yl)-9H-purin-6-yl]-benzamide 
• 132454-58-1 N-[9-((2S,3R,4S)-3,4-Bis-benzyloxymethyl-oxetan-2-yl)-9H-purin-6-yl]-benzamide 
• 120567-27-3 ((2S,3S,4S)-3,4-Bis-benzyloxymethyl-oxetan-2-yl)-methanol 
• 146820-71-5 (2S,3R,4S)-3,4-Bis-benzyloxymethyl-oxetane-2-carboxylic acid 

Relevant academic research and scientific papers

Synthesis of (t-2-Benzyloxymethyl-t-3-hydroxy-r-1-methoxycarbonyl)-tetrahydrofuran from an arabino-Lactone Triflate with K2CO3-MeOH

The arabino-lactone triflate 4 reacts with K2CO3 in MeOH to give the oxetane ester 5 and the tetrahydrofuran ester 6 in a ratio dependent upon the reaction temperature.

SYNTHESIS OF OXETANOCIN

A low yield synthesis of oxetanocin and its α-epimer by reaction of adenine with a protected 3-hydroxymethyl-2-chlorooxetane is described; attempts to synthesise other C-2'alkyl analogues of oxetanocin by analogous reactions indicate a limitation of this strategy for the synthesis of oxetane nucleosides.An intermediate for the synthesis of C-nucleoside analogues of oxetanocin is reported.

Ring contraction of 3-deoxy-2-O-trifluoromethanesulphonates of α-hydroxy-γ-lactones to oxetanes

The ring contraction of α-triflates of 3-deoxy-1,4-lactones bearing hydrogen or alkyl substituents in the 3-position to methyl oxetane-2-carboxylates on treatment with potassium carbonate in methanol is described.