54503-64-9

Basic information

• Product Name: 2,2-dimethyl-6-(trityloxymethyl)tetrahydrofuro[3,4-d][1,3]dioxol-4-ol
• Synonyms: 2,2-dimethyl-6-(trityloxymethyl)tetrahydrofuro[3,4-d][1,3]dioxol-4-ol
• CAS NO: 54503-64-9
• Molecular Weight: 432.516
• Mol File: 54503-64-9.mol
• Article Data: 23

Chemical Properties

• CAS DataBase Reference: 2,2-dimethyl-6-(trityloxymethyl)tetrahydrofuro[3,4-d][1,3]dioxol-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-dimethyl-6-(trityloxymethyl)tetrahydrofuro[3,4-d][1,3]dioxol-4-ol(54503-64-9)
• EPA Substance Registry System: 2,2-dimethyl-6-(trityloxymethyl)tetrahydrofuro[3,4-d][1,3]dioxol-4-ol(54503-64-9)

Safety Data

• Hazardous Substances Data: 54503-64-9(Hazardous Substances Data)

Upstream product

• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 76-83-5 trityl chloride 
• 106886-17-3 2,3-O-isopropylidene-5-O-triphenylmethyl-D-ribono-1,4-lactone 
• 32445-75-3 D-Ribose 
• 70266-87-4 6-hydroxymethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol 
• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 50-69-1 D-ribose 

Downstream Products

• 155968-87-9 (R)-1-[(4R,5S)-5-((S)-Hydroxy-pyridin-2-yl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-trityloxy-ethanol 
• 156128-73-3 2-(1S-2,3-O-isopropylidene-5-O-triphenylmethyl-D-ribo-pentitol-1-yl)benzothiophene 
• 155968-85-7 2-(1R-2,3-O-isopropylidene-5-O-triphenylmethyl-D-ribo-pentitol-1-yl)benzothiophene 
• 86563-09-9 (3ξ)-4,7-anhydro-1,3-dideoxy-3-bromo-5,6-O-isopropylidene-8-O-trityl-D-allo-oct-2-ulose 
• 86563-11-3 4,7-anhydro-1,3-dideoxy-3,3-dibromo-5,6-O-isopropylidene-8-O-trityl-D-allo-oct-2-ulose 
• 86563-07-7 (3ξ)-4,7-anhydro-1,3-dideoxy-3-chloro-5,6-O-isopropylidene-8-O-trityl-D-allo-oct-2-ulose 
• 83686-28-6 ethyl 4-(2′,3′-O-isopropylidene-5′-O-trityl-D-ribofuranosyl)-3-oxobutanoate 
• 83686-28-6 ethyl 4-(2′,3′-O-isopropylidene-5′-O-trityl-α-D-ribofuranosyl)-3-oxobutanoate 
• 83686-29-7 ethyl 4-(2′,3′-O-isopropylidene-5′-O-trityl-β-D-ribofuranosyl)-3-oxobutanoate 
• 129395-74-0 3-[1-[(4S,5R)-5-((R)-1-Hydroxy-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-meth-(Z)-ylidene]-5-methylene-piperidine-2,6-dione 
• 86563-12-4 methyl (2ξ)-3,6-anhydro-2-deoxy-2-chloro-4,5-O-isopropylidene-7-O-trityl-D-allo-heptonate 
• 86563-14-6 methyl (2ξ)-3,6-anhydro-2-deoxy-2-bromo-4,5-O-isopropylidene-7-O-trityl-D-allo-heptonate 
• 86563-25-9 methyl (Z)-2,3-dideoxy-2-bromo-4,5-O-isopropylidene-7-O-trityl-D-ribo-hept-2-enonate 
• 155968-86-8 2-(1S-2,3-O-isopropylidene-5-O-triphenylmethyl-D-ribo-pentitol-1-yl)indole 

Relevant articles and documents

Rhodium catalyzed stereospecific reductive carbocyclization of 1,6-enynes and synthesis of 4′-methyl-6′-substituted aristeromycins

The need of long-term treatment for chronic HBV, emergence of drug-resistant viruses and inefficiency of currently approved therapies to eliminate covalently closed circular DNA (cccDNA), mandates identification of potent and selective inhibitors of HBV replication with novel mechanisms of action. Entecavir, a carbocyclic guanosine nucleoside analog, is the most potent inhibitor of HBV replication on the market. Moreover, the naturally occurring carbocyclic nucleosides aristeromycin are known for their wide range of antiviral activities. In this research, we have utilized BINAP directed rhodium catalyzed reductive carbocyclization of 1,6-enynes (8a–b) through asymmetric hydrogenation which is an approach, not yet explored in carbocyclic sugar synthesis. Interestingly, we obtained exclusive anti-(9a) and Z-anti(9b) carbocyclic sugars. The new aristeromycin analogs (10a–b) with scaffold combination of entecavir and aristeromycin were then synthesized using the Mitsunobu reaction followed by deprotection.

POLYMORPHIC COMPOUNDS AND USES THEREOF

The present invention provides compounds and methods of use thereof for treatment of certain disorders and conditions, for example brain injuries such as stroke or traumatic brain injuries.

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.