34546-55-9

Basic information

• Product Name: 2-nitrobenzyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• Synonyms: 2-nitrobenzyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• CAS NO: 34546-55-9
• Molecular Weight: 483.429
• Mol File: 34546-55-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-nitrobenzyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-nitrobenzyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside(34546-55-9)
• EPA Substance Registry System: 2-nitrobenzyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside(34546-55-9)

Safety Data

• Hazardous Substances Data: 34546-55-9(Hazardous Substances Data)

Upstream product

• 612-25-9 2-Nitrobenzyl alcohol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 

Downstream Products

• 1581692-99-0 o-aminobenzyl β-D-glucopyranoside 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 

Relevant articles and documents

Synthesis of photolabile group protected anomeric acetals and its application in carbohydrate synthesis with the assistance of continuous flow photo-reactor

Selective deprotection of photolabile anomeric 2-nitrobenzyl acetals was achieved using continuous flow photo-reactor (UV radiation at 355 nm) in methanol-water. Various protecting groups such as acetyl, benzyl, benzoyl, benzylidine, TBS, etc. were found to be highly stable during the photolysis.

Synthetic studies toward c-glucosidic ellagitannins: A biomimetic total synthesis of 5-O-desgalloylepipunicacortein A

C-glucosidic ellagitannins constitute a subclass of bioactive polyphenolic natural products with strong antioxidant properties, as well as promising antitumoral and antiviral activities that are related to their capacity to interact with both functional and structural proteins. To date, most synthetic efforts toward ellagitannins have concerned glucopyranosic species. The development of a synthetic strategy to access C-glucosidic ellagitannins, whose characteristic structural feature includes an atropoisomeric hexahydroxydiphenoyl (HHDP) or a nonahydroxyterphenoyl (NHTP) unit that is linked to an open-chain glucose core by a C-aryl glucosidic bond, is described herein. The total synthesis of the biarylic HHDP-containing 5-O- desgalloylepipunicacortein A (1 β) was achieved by either using the natural ellagic acid bis-lactone as a precursor of the requested HHDP unit or by implementing an atroposelective intramolecular oxidative biarylic coupling to forge this HHDP unit. Both routes converged in the penultimate step of this synthesis to enable a biomimetic formation of the key C-aryl glucosidic bond in the title compound.