106248-68-4

Upstream product

• 488-81-3 Adonitol 
• 313484-66-1 (3R,4R,5R)-2-Methoxy-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan 
• 14520-34-4 methyl 2,3,5-tri-O-methyl-D-ribofuranoside 
• 14520-04-8 methyl 2,3,5-tri-O-methyl-D-ribofuranoside 
• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 532-20-7 D-Ribose 
• 7647-01-0 hydrogenchloride 
• 35320-17-3 D-ribitol-5-phosphate 
• 63493-94-7 (2RS)-2-hydroxymethyl-2,5-dihydrofuran 
• 87-99-0 XYLITOL 
• 58-86-6 D-xylose 
• 7643-75-6 L-(-)-arabitol 
• 5328-37-0 L-arabinose 
• 3325-26-6 1,4-anhydroarabinitol 2,3,5-triacetate 

Downstream Products

• 30591-86-7 tris-O-(toluene-4-sulfonyl)-2,5-anhydro-L-arabitol 
• 172489-96-2 Benzoic acid (2R,3S,4S)-3,4-dimethoxy-tetrahydro-furan-2-ylmethyl ester 
• 172489-94-0 Benzoic acid (2R,3S,4S)-4-methoxy-2-methoxymethyl-tetrahydro-furan-3-yl ester 
• 172489-92-8 Benzoic acid (3S,4R,5R)-4-methoxy-5-methoxymethyl-tetrahydro-furan-3-yl ester 
• 74720-63-1 1,5-anhydro-4,6-O-benzylidene-3-deoxy-3-nitro-D-glucitol 
• 203383-47-5 1-{(4aR,7S,8S,8aS)-8-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-5-methyl-1H-pyrimidine-2,4-dione 
• 203383-44-2 9-{(4aR,7S,8S,8aS)-8-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-9H-purin-6-ylamine 
• 203383-46-4 3-Benzoyl-1-{(4aR,7S,8S,8aS)-8-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-5-methyl-1H-pyrimidine-2,4-dione 
• 203797-25-5 1,5-anhydro-4,6-O-benzylidene-3-deoxy-3-nitro-D-allitol 
• 215445-56-0 (4aR,7R,8aS)-8-Hydroxymethyl-8-nitro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 203383-49-7 (4aR,8aS)-8-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine 
• 203383-42-0 (4aR,7R,8R,8aS)-8-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 203383-43-1 (4aR,7R,8S,8aS)-8-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 203383-40-8 (4aR,7R,8S,8aS)-8-[(4-Methoxy-phenyl)-diphenyl-methoxymethyl]-8-nitro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 

Relevant academic research and scientific papers

Reductive cleavage of permethylated polysaccharides with borane-methyl sulfide complex and butyltin trichloride

Several per-O-methylated monosaccharides and polysaccharides were used as models in an attempt to identify more convenient reagents for accomplishing reductive cleavage of glycosidic linkages. Included in the model studies were methyl α- and β-D-glucopyranoside, methyl α- and β-D-mannopyranoside, and methyl α- and β-D-ribofuranoside. These studies led to the identification of a new promoter, butyltin trichloride, for carrying out reductive cleavage when borane-methyl sulfide complex was used as the reducing agent. These reagents were found to accomplish the reductive cleavage of per-O-methylated amylose, cellulose, and pullulan to give only the expected derivatives of 1,5-anhydro-D-glucitol. These reagents also accomplished reductive cleavage of per-O-methylated inulin to give only the expected derivatives of 2,5-anhydro-D-mannitol and 2,5-anhydro-D-glucitol. Reductive cleavage using these reagents is easy to perform, and subsequent acetylation of the products is readily accomplished in situ.

Controlling Sugar Deoxygenation Products from Biomass by Choice of Fluoroarylborane Catalyst

The feedstocks from biomass are defined and limited by nature, but through the choice of catalyst, one may change the deoxygenation outcome. We report divergent but selective deoxygenation of sugars with triethylsilane (TESH) and two fluoroarylborane catalysts, B(C6F5)3 and B(3,5-CF3)2C6H3)3 (BAr3,5-CF3). To illustrate, persilylated 2-deoxyglucose shows exocyclic C-O bond cleavage/reduction with the less sterically congested BAr3,5-CF3, whereas endocyclic C-O bond cleavage/reduction predominates with the more Lewis acidic B(C6F5)3. Chiral furans and linear polyols can be selectively synthesized depending on the catalysts. Mechanistic studies demonstrate that the resting states of these catalysts are different.

Transfer hydrogenation as a redox process in nucleotides

Using a combined theoretical and experimental strategy, the heats of hydrogenation of the nucleotide bases uracil, thymine, cytosine, adenine, and guanine have been determined. The most easily hydrogenated base is uracil, followed by thymine and cytosine. Comparison of these hydrogenation enthalpies with those of ketones and aldehydes derived from sugar models indicates the possibility of near-thermoneutral hydrogen transfer between uracil and the sugar phosphate backbone in oligonucleotides. (Figure Presented)

Synthesis and structure of selected quaternary N-(1,4-anhydro-5-deoxy-2,3- O-isopropylidene-D,L-ribitol-5-yl)ammonium salts

The syntheses have been developed for quaternary N-(1,4-anhydro-5-deoxy-2, 3-O-isopropylidene-d,l-ribitol-5-yl)ammonium salts derived from five aromatic amines, pyridine, 2-methylpyridine, 3-carbamoylpyridine, 4-(N,N-dimethylamino) pyridine, and quinoline, as well as two tertiary aliphatic amines, trimethylamine and triethylamine. Reactions of 1,4-anhydro-2,3-O-isopropylidene- 5-O-tosyl-d,l-ribitol with tri-n-propylamine and tri-n-butylamine were unsuccessful. The products were identified on the basis of their 1H and 13C NMR spectra. The structure of N-(1,4-anhydro-5-deoxy-2,3-O- isopropylidene-d,l-ribitol-5-yl)trimethylammonium tosylate was additionally elucidated by X-ray diffractometry.

Solvent-free thermal dehydration of pentitols on zeolites

Dehydration of D-arabinitol, ribitol, and xylitol at high temperature in the presence of molecular sieves without solvent in an argon atmosphere is described. Products arising after the dehydration-cyclization (cyclodehydration) reaction with retention or inversion of the configuration of asymmetric carbon atoms, were observed. Complete analytical separations of exhaustively O-acetylated reaction products were achieved by means of GC. The chemical structures of the compounds obtained were assigned using co-injection with standards. Copyright

Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses

L-Arabinose is an abundant resource available as a waste product of the sugar beet industry. Through use of a hydrazone-based strategy, L-arabinose was selectively dehydrated to form a chiral tetrahydrofuran on a multi-gram scale without the need for protecting groups. This approach was extended to other biomass-derived reducing sugars and the mechanism of the key cyclization investigated. This methodology was applied to the synthesis of a range of functionalized chiral tetrahydrofurans, as well as a formal synthesis of 3R-3-hydroxymuscarine.

Hydrodeoxygenation of C4-C6 sugar alcohols to diols or mono-alcohols with the retention of the carbon chain over a silica-supported tungsten oxide-modified platinum catalyst

The hydrodeoxygenation of erythritol, xylitol, and sorbitol was investigated over a Pt-WOx/SiO2 (4 wt% Pt, W/Pt = 0.25, molar ratio) catalyst. 1,4-Butanediol can be selectively produced with 51% yield (carbon based) by erythritol hydrodeoxygenation at 413 K, based on the selectivity over this catalyst toward the regioselective removal of the C-O bond in the -O-C-CH2OH structure. Because the catalyst is also active in the hydrodeoxygenation of other polyols to some extent but much less active in that of mono-alcohols, at higher temperature (453 K), mono-alcohols can be produced from sugar alcohols. A good total yield (59%) of pentanols can be obtained from xylitol, which is mainly converted to C2 + C3 products in the literature hydrogenolysis systems. It can be applied to the hydrodeoxygenation of other sugar alcohols to mono-alcohols with high yields as well, such as erythritol to butanols (74%) and sorbitol to hexanols (59%) with very small amounts of C-C bond cleavage products. The active site is suggested to be the Pt-WOx interfacial site, which is supported by the reaction and characterization results (TEM and XAFS). WOx/SiO2 selectively catalyzed the dehydration of xylitol to 1,4-anhydroxylitol, whereas Pt-WOx/SiO2 promoted the transformation of xylitol to pentanols with 1,3,5-pentanetriol as the main intermediate. Pre-calcination of the reused catalyst at 573 K is important to prevent coke formation and to improve the reusability.

IONIZABLE LIPIDS FOR NUCLEIC ACID DELIVERY

The present document describes compounds, or pharmaceutically acceptable salt thereof, of a core formula (I) Wherein R1 includes an amino group. These compounds are particularly useful in the formulation and in vivo and ex vivo delivery of nucleic acid and protein therapeutics for preparing and implementing T cell transfection, gene editing, cancer therapies, cancer prophylactics, and in the preparation of vaccines.

S-ANTIGEN TRANSPORT INHIBITING OLIGONUCLEOTIDE POLYMERS AND METHODS

Various embodiments provide STOPS? polymers that are S-antigen transport inhibiting oligonucleotide polymers, processes for making them and methods of using them to treat diseases and conditions. In some embodiments the STOPS? modified oligonucleotides include an at least partially phosphorothioated sequence of alternating A and C units having modifications as described herein. The sequence independent antiviral activity against hepatitis B of embodiments of STOPS? modified oligonucleotides, as determined by HBsAg Secretion Assay, is an EC50 that is less than 100 nM.

Synthesis of novel carbohydrate based pyridinium ionic liquids and cytotoxicity of ionic liquids for mammalian cells

The large pool of naturally occurring carbohydrates with their diversity in chirality and structure led to the idea of a systematic investigation of carbohydrate based ILs. To this end, we investigated the influence of different ether groups, mainly methyl or ethyl ether, on the secondary OH groups as well as different configurations on physical properties such as melting point, thermostability and especially the influence on cell toxicity. For this investigation we chose α- and β-methyl-, β-allyl- and β-phenyl d-glucopyranose as well as four 1-deoxy-pentoses. In order to be able to classify the results, more ionic liquids with different structural motives were examined for cytotoxicity. Here, we present data that confirm the biocompatibility of such ILs consisting of naturally occurring molecules or their derivatives. The synthesized carbohydrate based ILs were tested for their suitability as additives in coatings for medical applications such as drug-eluting balloons.