96212-44-1

Upstream product

• 1826-67-1 vinyl magnesium bromide 
• 100-39-0 benzyl bromide 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-ribo-3-hexulofuranose 
• 39838-77-2 (3aR,5R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol 
• 51996-47-5 (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]-dioxol-6-ol 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 77-76-9 2,2-dimethoxy-propane 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 2595-05-3 Diacetone D-glucose 
• 582-52-5 1,2:5,6-diacetone-D-glucose 

Downstream Products

• 96212-45-2 (R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol 
• 136153-00-9 (3aR,4aS,7aS,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-one 
• 1227269-86-4 (3aR,4aR,5R,7aR,7bR)-7a-(benzyloxy)-2,2-dimethylhexahydro-5H-cyclopenta[4,5]furo[2,3-d][1,3]dioxol-5-ol 

Relevant academic research and scientific papers

Development of a Flexible and Robust Synthesis of Tetrahydrofuro[3,4- b]furan Nucleoside Analogues

In the context of a PRMT5 inhibitor program, we describe our efforts to develop a flexible and robust strategy to access tetrahydrofuro[3,4-b]furan nucleoside analogues. Ultimately, it was found that a Wolfe type carboetherification from an alkenol derive

The Discovery of Two Novel Classes of 5,5-Bicyclic Nucleoside-Derived PRMT5 Inhibitors for the Treatment of Cancer

Protein arginine methyltransferase 5 (PRMT5) is a type II arginine methyltransferase that catalyzes the post-translational symmetric dimethylation of protein substrates. PRMT5 plays a critical role in regulating biological processes including transcriptio

PRMT5 INHIBITORS

The present invention provides a compound of Formula (I) and the pharmaceutically acceptable salts, esters, and prodrugs thereof, which are PRMT5 inhibitors. Also provided are methods of making compounds of Formula I, pharmaceutical compositions comprising compounds of Formula I, and methods of using these compounds to treat cancer, sickle cell, and hereditary persistence of foetal hemoglobin (HPFH) mutations.

Synthesis of fused cyclic systems containing medium-sized rings through tandem ROM-RCM of norbornene derivatives embedded in a carbohydrate template

A general approach for the synthesis of fused cyclic systems containing medium-sized rings (7-9) has been developed. The key steps involve a diastereoface-selective Diels-Alder reaction of the dienophiles 4a-d attached to a furanosugar with cyclopentadiene and ring opening (ROM)-ring closing metathesis (RCM) of the resulting norbornene derivatives 10a-d and 11a-d. Diels-Alder reaction of the dienophiles 4a-d with cyclopentadiene in the absence of a catalyst produced 10a-d as the major product arising through addition of the diene to the unhindered Si-face. The most interesting and new aspect of the Diels-Alder reaction of these dienophiles is the accessibility of the Re-face that was blocked by the alkenyl chains under Lewis acid catalysis producing the diastereoisomers 11a-d exclusively. The reversal of facial selectivity from an uncatalyzed reaction to a catalyzed one is unprecedented. The observed stereochemical dichotomy is attributed to rotation of the enone moiety along the o bond linking the sugar moiety during formation of the chelate 13. This makes the Re-face of the enone moiety in 4a-d unhindered. Diels-Alder reaction of the carbocyelic analogue 15 under Lewis acid catalysis produced a 1:1 mixture of the adducts 16 and 17 confirming the participation of sugar ring oxygen in chelate formation. Finally ROM-RCM of 10a-d and 11a-d with Grubbs' catalyst afforded the cis-syn-cis and cis-anti-cis bicyclo-annulated sugars 21a-d and 23a-d, respectively, containing 7-9 membered rings.

Synthesis of bicyclic nucleosides by ring-closing metathesis

The ring-closing metathesis method is applied in the construction of conformationally restricted bicyclic nucleosides. From diacetone-D-glucose, the unsaturated bicyclic carbohydrate derivative 11 is efficiently obtained through two vinyl group Grignard a

Rhodium (I)-catalyzed cyclizations of 3-C-alkenyl pentodialdose derivatives

Cyclization of 1,2-isopropylidene 3-C-allyl ribo-pentodialdose, and 1-methylallyl and 3-C-vinyl analogs, with [(Ph3P)2RhCl]2 under CH2CH2 leads to intramolecular hydroacylation of the alkene with sele

The Oxahydrindene Component of the Avermectins

An intramolecular nitrile oxide cycloaddition involving a vinyl group at C3 and a nitrile oxide at C6 of a derivative of diacetone glucose provides a route to the oxahydrindene 2 stereochemically pure and appropriately functionalized for further elaboration.