84709-46-6

Basic information

• Product Name: 2,3-O-isopropylidene-5-O-(triphenylmethyl)-D-ribitol
• Synonyms: 2,3-O-isopropylidene-5-O-(triphenylmethyl)-D-ribitol
• CAS NO: 84709-46-6
• Molecular Weight: 434.532
• Mol File: 84709-46-6.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 2,3-O-isopropylidene-5-O-(triphenylmethyl)-D-ribitol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-O-isopropylidene-5-O-(triphenylmethyl)-D-ribitol(84709-46-6)
• EPA Substance Registry System: 2,3-O-isopropylidene-5-O-(triphenylmethyl)-D-ribitol(84709-46-6)

Safety Data

• Hazardous Substances Data: 84709-46-6(Hazardous Substances Data)

Upstream product

• 76-83-5 trityl chloride 
• 3969-84-4 3,4-di-O-isopropylidene-D-mannitol 
• 84608-23-1 3,4-O-isopropylidene-1-O-trityl-D-mannitol 
• 113626-56-5 (2S,3S,4S)-2,3-dihydroxy-4-trityloxymethyl-4-butanolide 
• 101758-68-3 (R)-(+)-5-triphenylmethyloxymethyl-2 (5H)-furanone 
• 5336-08-3 D-Ribono-1,4-lactone 
• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 532-20-7 D-Ribose 
• 106886-17-3 2,3-O-isopropylidene-5-O-triphenylmethyl-D-ribono-1,4-lactone 
• 113571-56-5 (2S,3S,4S)-2,3-isopropylidenedioxy-4-trityloxymethyl-4-butanolide 
• 54503-64-9 2,3-O-isopropylidene-5-O-trityl-D-ribofuranose 
• 55726-19-7 2,3-O-Isopropylidene-5-O-trityl-D-ribofuranose 

Downstream Products

• 88559-47-1 2,2-Dimethyl-propionic acid (4S,5R)-5-((R)-1-hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 132430-67-2 2,3-O-Isopropylidene-1,4-di-O-methanesulfonyl-5-O-trityl-D-ribitol 
• 84608-25-3 Toluene-4-sulfonic acid (4S,5R)-5-((R)-1-hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 84608-25-3 Toluene-4-sulfonic acid (4R,5R)-5-((R)-1-hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 162635-55-4 1,4-anhydro-2,3-O-isopropylidene-5-O-(triphenylmethyl)-D-ribitol 
• 420793-10-8 1,4-di-O-benzoyl-2,3-O-isopropylidene-5-O-trityl-D-ribitol 
• 278180-12-4 2,5-di-O-benzoyl-3,4-O-isopropylidene-aldehydo-L-ribose 
• 278180-11-3 1,4-di-O-benzoyl-2,3-O-isopropylidene-D-ribitol 
• 173009-66-0 1,2-di-O-acetyl-3,5-di-O-benzoyl-β-L-ribofuranose 
• 84773-09-1 1,4-anhydro-2,3-O-isopropylidene-5-O-toluene-p-sulphonyl-D-ribitol 
• 69434-51-1 1-(Adenin-9-yl)-1-deoxy-D-arabitol 
• 88559-49-3 {(4S,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-trityloxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol 
• 88559-55-1 {2-[(4R,5S)-2,2-Dimethyl-5-(2-trityloxy-acetyl)-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester 
• 88559-54-0 {2-[(4R,5R)-5-((R)-1-Hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester 

Relevant articles and documents

Synthesis of Terminal Ribose Analogues of Adenosine 5′-Diphosphate Ribose as Probes for the Transient Receptor Potential Cation Channel TRPM2

TRPM2 (transient receptor potential cation channel, subfamily M, member 2) is a nonselective cation channel involved in the response to oxidative stress and in inflammation. Its role in autoimmune and neurodegenerative diseases makes it an attractive pharmacological target. Binding of the nucleotide adenosine 5′-diphosphate ribose (ADPR) to the cytosolic NUDT9 homology (NUDT9H) domain activates the channel. A detailed understanding of how ADPR interacts with the TRPM2 ligand binding domain is lacking, hampering the rational design of modulators, but the terminal ribose of ADPR is known to be essential for activation. To study its role in more detail, we designed synthetic routes to novel analogues of ADPR and 2′-deoxy-ADPR that were modified only by removal of a single hydroxyl group from the terminal ribose. The ADPR analogues were obtained by coupling nucleoside phosphorimidazolides to deoxysugar phosphates. The corresponding C2″-based analogues proved to be unstable. The C1″- and C3″-ADPR analogues were evaluated electrophysiologically by patch-clamp in TRPM2-expressing HEK293 cells. In addition, a compound with all hydroxyl groups of the terminal ribose blocked as its 1″-β-O-methyl-2″,3″-O-isopropylidene derivative was evaluated. Removal of either C1″ or C3″ hydroxyl groups from ADPR resulted in loss of agonist activity. Both these modifications and blocking all three hydroxyl groups resulted in TRPM2 antagonists. Our results demonstrate the critical role of these hydroxyl groups in channel activation.

Syntheses of cyclopentyl nucleoside (?)-neplanocin A through tetrazole-fragmentation from cyanophosphates

We recently reported a novel synthetic method for five-membered unsaturated cyclic compounds from ketones involving cyanophosphates (CPs) under neutral conditions, in which alkylidene carbenes generated through tetrazole-fragmentation undergo [1,5]-C–H in

Synthesis of enantiomerically pure 4-substituted riboses

An efficient and flexible synthesis of 4-substituted ribose analogues is described. The key step involves the simple addition of a Grignard reagent to a ketone derived from a commercially available ribose. The addition of a range of Grignard reagents proc