200346-53-8

Upstream product

• 19614-12-1 2-bromo-5-methoxybenzyl bromide 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 866890-75-7 (3aR,5S,6R,6aR)-6-(2-bromo-5-methoxy-benzyloxy)-5-iodomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 1030614-10-8 (3aR,5R,6S,6aR)-[6-(2-bromo-5-methoxybenzyloxy)-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]methanol 
• 866890-78-0 (3aR,6R,6aR)-6-(2-bromo-5-methoxy-benzyloxy)-2,2-dimethyl-5-methylene-tetrahydro-furo[2,3-d][1,3]dioxole 
• 200346-55-0 (R)-1-[(3aR,5R,6S,6aR)-6-(2-Bromo-5-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethane-1,2-diol 

Relevant academic research and scientific papers

Palladium-catalyzed intramolecular C-O bond formation: An approach to the synthesis of chiral benzodioxocines

Palladium-catalyzed intramolecular aryl etherification using bulky binaphthylphosphane or bis(diphenylphosphanyl)ferrocene ligands is shown to be a convenient method for the synthesis of eight-membered oxygen heterocycles. Application of this methodology to a sugar derivative led to the synthesis of chiral benzodioxocine. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Radical cyclization of exo-methylene furanose derivatives: An expedient approach to the synthesis of chiral tricyclic nucleosides and benzannulated oxepine derivatives

Tributyltin radical mediated cyclization of the glucose derived exo-methylene furanose derivatives 5a-c led to the highly functionalized cis-fused bicyclic ethers 6a-c. The product could subsequently be transformed to the optically active tricyclic nucleoside analogue 8 or oxepine derivative 9.

Synthesis of chiral cis- and trans-furo[3,2-c][2]benzoxocines from D-glucose by regioselective 8-endo aryl radical cyclisation

A simple chiral synthesis of cis- and trans-furo[3,2-c][2]benzoxocines 8a-d and 9a-d through a regioselective 8-endo-trig aryl radical cyclisation of the respective 5,6-dideoxy-D-xylo-hex-5-enofuranosides 6a-d and 5,6-dideoxy-D-ribo-hex-5-enofuranosides 7

A simple construction of chiral fused benzoxocine ring ethers from D-glucose by regioselective 8-endo-aryl radical cyclisation

A regioselective 8-endo-trig aryl radical cyclisation of the 5,6-deoxy-D-xylo-5-enofuranosides 3a and 3b with tri-n-butyltin hydride provides the chiral furo[3,2-c][2]benzoxocines 4a and 4b in good yields; the crystal structure of 4a is reported.