96212-45-2

Upstream product

• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 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 
• 100-39-0 benzyl bromide 
• 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 
• 96212-44-1 (3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro-[2,3-d][1,3]dioxole 

Downstream Products

• 801316-38-1 C₃₄H₃₆O₈ 
• 96212-56-5 (3aR,4aR,5R,8S,8aR,8bR)-8a-Benzyloxy-5-methoxy-2,2,6-trimethyl-8-trityloxymethyl-3a,4a,5,8,8a,8b-hexahydro-benzo[4,5]furo[2,3-d][1,3]dioxole 
• 96212-58-7 2,2-Dimethyl-propionic acid (1S,4R,5R,6S)-6-benzyloxy-6-((S)-1,2-dihydroxy-ethyl)-5-hydroxy-4-methoxy-3-methyl-cyclohex-2-enylmethyl ester 
• 96212-59-8 2,2-Dimethyl-propionic acid (3S,3aS,4S,7R,7aR)-3a-benzyloxy-3-hydroxy-7-methoxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester 
• 96227-27-9 ((3aR,4aR,5R,8S,8aR,8bR)-8a-Benzyloxy-5-methoxy-2,2,6-trimethyl-3a,4a,5,8,8a,8b-hexahydro-benzo[4,5]furo[2,3-d][1,3]dioxol-8-yl)-methanol 
• 457068-06-3 Acetic acid 2-[(2S,3S,4R,5R)-3-benzyloxy-2-benzyloxymethyl-4-(1-methoxy-1-methyl-ethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl]-ethyl ester 
• 457068-04-1 2'-O-acetyl-3'-C-acetyloxyethyl-3',5'-di-O-benzyl-5-methyl-4'-C-(p-toluenesulfonyloxymethyl)uridine 
• 457068-07-4 Toluene-4-sulfonic acid (2S,3S,4R,5R)-3-benzyloxy-2-benzyloxymethyl-3-(2-hydroxy-ethyl)-4-(1-methoxy-1-methyl-ethoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 457068-05-2 3'-C-acetyloxyethyl-3',5'-di-O-benzyl-5-methyl-4'-C-(p-toluenesulfonyloxymethyl)uridine 
• 457068-03-0 1,2-di-O-acetyl-3-C-acetoxyethyl-3,5-di-O-benzyl-4-C-(p-toluenesulfonyloxymethyl)-D-ribofuranose 
• 457068-12-1 3-N-benzyloxymethyl-3',5'-di-O-benzyl-2'-O-methyl-5-methyl-3'-C,4'-C-ethoxymethyleneuridine 
• 457068-11-0 5-methyl-3-N-benzyloxymethyl-3',5'-di-O-benzyl-3'-C,4'-C-ethoxymethyleneuridine 
• 457068-08-5 1-[(2R,3R,3aS,7aR)-3a-Benzyloxy-7a-benzyloxymethyl-3-(1-methoxy-1-methyl-ethoxy)-hexahydro-furo[2,3-c]pyran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 

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

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 and properties of trans-3′,4′-bridged nucleic acids having typical S-type sugar conformation

The synthesis of nucleoside analogues with a conformationally restricted sugar moiety is of great interest. The present research describes the synthesis of BNA (bridged nucleic acid) monomers 1 and 2 bearing a 4,7-dioxabicyclo[4.3.0] nonane skeleton and a methoxy group at the C2' position. Conformational analysis showed that the sugar moiety of these monomers is restricted in a typical S-type conformation. It was difficult to synthesize the phosphoramidite derivative of the ribo-type monomer 1, while the phosphoramidite of the arabino-type monomer 2 was successfully prepared and incorporated into oligodeoxynucleotides (ODNs). The hybridization ability of the obtained ODN derivatives containing 2 with complementary strands was evaluated by melting temperature (Tm) measurements. As a result, the ODN derivatives hybridized with DNA and RNA complements in a sequence-selective manner, though the stability of the duplexes was lower than that of the corresponding natural DNA/DNA or DNA/RNA duplex.

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.