118967-96-7

Basic information

• Product Name: ((3aR,4R,6aR)-6-bromo-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-yl)methyl benzoate
• Synonyms: ((3aR,4R,6aR)-6-bromo-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-yl)methyl benzoate
• CAS NO: 118967-96-7
• Molecular Weight: 357.201
• Mol File: 118967-96-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: ((3aR,4R,6aR)-6-bromo-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-yl)methyl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: ((3aR,4R,6aR)-6-bromo-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-yl)methyl benzoate(118967-96-7)
• EPA Substance Registry System: ((3aR,4R,6aR)-6-bromo-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-yl)methyl benzoate(118967-96-7)

Safety Data

• Hazardous Substances Data: 118967-96-7(Hazardous Substances Data)

Upstream product

• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 2857-97-8 trimethylsilyl bromide 
• 532-20-7 D-Ribose 
• 5517-60-2 methyl 3'-O-benzoyl-2,3-O-isopropylidene-β-D-apiofuranoside 

Downstream Products

• 5517-60-2 methyl 3'-O-benzoyl-2,3-O-isopropylidene-β-D-apiofuranoside 
• 118967-97-8 methyl-5-O-benzoyl-2,3-O-isopropylidene-α-D-ribofuranoside 
• 118968-00-6 3-O-(5-O-benzoyl-2,3-O-isopropylidene-α-D-ribofuranosyl)-1,2-5,6-di-O-isopropylidene-α-D-glucofuranose 
• 118968-01-7 6-O-(5-O-benzoyl-2,3-O-isopropylidene-α-D-ribofuranosyl)-1,2-5,6-di-O-isopropylidene-α-D-glucofuranose 
• 118967-98-9 methyl 5-O-(5-O-benzoyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-2,3-O-isopropylidene-β-D-ribofuranoside 
• 118967-99-0 methyl 5-O-(5-O-benzoyl-2,3-O-isopropylidene-α-D-ribofuranosyl)-2,3-O-isopropylidene-β-D-ribofuranoside 

Relevant articles and documents

Chemoselective and Diastereoselective Synthesis of C-Aryl Nucleoside Analogues by Nickel-Catalyzed Cross-Coupling of Furanosyl Acetates with Aryl Iodides

Canonical nucleosides are vulnerable to enzymatic and chemical degradation, yet their stable mimics—C-aryl nucleosides—have demonstrated potential utility in medicinal chemistry, chemical biology, and synthetic biology, although current synthetic methods remain limited in terms of scope and selectivity. Herein, we report a cross-electrophile coupling to prepare C-aryl nucleoside analogues from readily available furanosyl acetates and aryl iodides. This nickel-catalyzed modular approach is characterized by mild reaction conditions, broad substrate scope, excellent β-selectivity, and high functional-group compatibility. The exclusive chemoselectivity with respect to the aryl iodide enables efficient preparation of a variety of C-aryl halide furanosides suitable for various downstream transformations. The practicality of this transformation is demonstrated through the synthesis of a potent analogue of a naturally occurring NF-κB activator.

A Simple Synthesis of α-D-Ribofuranosides

The glycosylation of various aglycones with 5-O-benzoyl-2,3-O-isopropylidene-β-D-ribofuranosyl bromide (2) has been studied under different reaction conditions.It is possible to obtain high yields of α-linked ribofuranosides using methanol or methyl-2,3-O