85950-35-2

Upstream product

• 67-63-0 isopropyl alcohol 
• 15919-16-1 5-β-formyl-4-β-O-tosyl-2α,3α-O-isopropylidenetetrahydrofuran 
• 3253-75-6 1,2:5,6-di-O-isopropylidene-3-O-tosyl-α-D-glucofuranoside 
• 2946-01-2 (3aR,5R,6S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 101068-03-5 methyl (methyl 3-O-toluene-p-sulphonyl-α-D-xylofuranosid)uronate 
• 124516-87-6 methyl (methyl 3-O-tosyl-β-D-xylofuranosid)uronate 
• 101068-02-4 4-O-acetyl-1,2-O-isopropylidene-3-O-toluene-p-sulphonyl-α-D-xylopyranurono-5,1-lactone 
• 129511-00-8 ethyl 1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-xylofuranuronate 
• 87910-48-3 N⁶-(3-O-p-tolylsulfonyl-1,2-O-isopropylidene-α-D-xylofuranoyl)adenine 
• 124516-97-8 (4R)-2-(2-benzyloxyethyl)-4-(dimethyl-t-butylsilyloxy)cyclopent-2-enone 
• 124516-96-7 (2R)-7-benzyloxy-2-(dimethyl-t-butylsilyloxy)-4-oxoheptanal 
• 124516-95-6 (4R,5R)-2-(3-benzyloxypropyl)-4-(dimethyl-t-butylsilyloxy)-4,5-dihydro-5-methoxyfuran 
• 85950-36-3 (3aR,5S,6R,6aR)-methyl 2,2-dimethyl-6-(tosyloxy)tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylate 

Relevant academic research and scientific papers

C-3 epimers of sugar amino acids as foldameric building blocks: improved synthesis, useful derivatives, coupling strategies

To obtain key sugar derivatives for making homooligomeric foldamers or α/β-chimera peptides, economic and multigram scale synthetic methods were to be developed. Though described in the literature, the cost-effective making of both 3-amino-3-deoxy-ribofuranuronic acid (H–tX–OH) and its C-3 epimeric stereoisomer, the 3-amino-3-deoxy-xylofuranuronic acid (H–cX–OH) from d-glucose is described here. The present synthetic route elaborated is (1) appropriate for large-scale synthesis; (2) reagent costs reduced (e.g. by a factor of 400); (3) yields optimized are ~80% or higher for all six consecutive steps concluding –tX– or –cX– and (4) reaction times shortened. Thus, a new synthetic route step-by-step optimized for yield, cost, time and purification is given both for d-xylo and d-ribo-amino-furanuronic acids using sustainable chemistry (e.g. less chromatography with organic solvents; using continuous-flow reactor). Our study encompasses necessary building blocks (e.g. –X–OMe, –X–OiPr, –X–NHMe, Fmoc–X–OH) and key coupling reactions making –Aaa–tX–Aaa– or –Aaa–tX–tX–Aaa– type “inserts”. Completed for both stereoisomers of X, including the newly synthesized Fmoc–cX–OH, producing longer oligomers for drug design and discovery is more of a reality than a wish.

The carbohydrate-sesquiterpene interface. Directed synthetic routes to both (+)- and (-)-fomannosin from D-glucose

(Chemical Equation Presented) An enantiodivergent strategy for the total chemical synthesis of both naturally occurring (+)-fomannosin (1) and its (-)-antipode (ent-1) from α-D-glucose has been developed and successfully implemented. The key steps in the

The nature of the diastereotopy in the methylene and methyl protons of the ethyl and isopropyl esters of uronic acids

It was shown that the anisochromism of the diastereotopic geminal methylene and methyl protons in the ethyl and isopropyl esters of uronic acids in the PMR spectra is due to the presence of anisotropic groups in the chiral molecule and depends on the distance between the alkoxycarbonyl and the anisotropic group and on their orientation in relation to each other in space.In the case where the carbonyl of the alkoxycarbonyl group lies in the same plane as the heterocycle of the purine or pyrimidine series the geminal diastereotopic methylene and methyl protons become isochronous in the PMR spectra as a result of the formation of an intramolecular hydrogen bond between the H2, H8, and H6 protons of the heterocycles and the alkoxycarbonyl.