200346-52-7

Upstream product

• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 

Downstream Products

• 866890-77-9 (3aR,6R,6aR)-6-(2-bromo-benzyloxy)-2,2-dimethyl-5-methylene-tetrahydro-furo[2,3-d][1,3]dioxole 
• 1030614-06-2 (3aR,5R,6S,6aR)-[6-(2-bromobenzyloxy)-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]methanol 
• 866890-74-6 (3aR,5S,6R,6aR)-6-(2-bromo-benzyloxy)-5-iodomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 1402436-25-2 6-(2-bromobenzyloxy)-2,2-dimethyl-5-prop-2-ynyloxymethyltetrahydrofuro[2,3-d][1,3]dioxole 
• 1402436-26-3 1-[6-(2-bromobenzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-trityloxyethanol 
• 1402436-28-5 6-(2-bromobenzyloxy)-2,2-dimethyl-5-(1-prop-2-ynyloxy-2-trityloxyethyl)tetrahydrofuro[2,3-d][1,3]dioxole 
• 1402436-30-9 5-(1-benzyloxy-2-trityloxyethyl)-6-(2-bromobenzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole 
• 1402436-31-0 2-benzyloxy-2-[6-(2-bromobenzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethanol 
• 918795-09-2 2-{(S)-[(3aR,5R,6S,6aR)-6-(2-bromo-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-hydroxy-methyl}-acrylic acid ethyl ester 
• 918795-05-8 2-{(R)-[(3aR,5R,6S,6aR)-6-(2-bromo-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-hydroxy-methyl}-acrylic acid ethyl ester 
• 918795-06-9 2-{(S)-[(3aR,5R,6S,6aR)-6-(2-bromo-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-hydroxy-methyl}-acrylic acid methyl ester 
• 918795-02-5 2-{(R)-[(3aR,5R,6S,6aR)-6-(2-bromo-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-hydroxy-methyl}-acrylic acid methyl ester 
• 918794-98-6 2-{[(3aR,5R,6S,6aR)-6-(2-Bromo-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-hydroxy-methyl}-acrylonitrile 

Relevant academic research and scientific papers

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.

Intramolecular base-free sonogashira reaction for the synthesis of benzannulated chiral macrocycles embedded in carbohydrate templates

A base-free, intramolecular Sonogashira reaction-based general approach has been established for the diversity-oriented synthesis (DOS) of fused bi- and tricyclic systems containing benzannulated, 10- to 13-membered chiral macrocycles embedded in carbohydrate templates. Macrocycles with different ring sizes have been prepared by pre-designing the chiral building blocks. Base-sensitive groups like acetyl and TBDPS survived the reaction conditions. Copyright

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.

Sequential Baylis-Hillman reaction and radical cyclization of furanose derivatives: expeditious approach to enantiopure benzo-fused nine-membered oxacycles

A regioselective 9-endo-trig aryl radical cyclization of d-glucose derived diastereomeric Baylis-Hillman reaction products with Bu3SnH led to highly functionalized tricyclic benzannulated ethers incorporating cis- and trans-9,5 bicyclic systems

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