84366-59-6

Upstream product

• 102794-46-7 Carbonic acid allyl ester (2S,3R,4R)-4-allyloxy-2,3,5-tris-benzyloxy-pentyl ester 
• 64363-77-5 methyl 2,3,5-tri-O-benzyl-D-ribofuranoside 
• 532-20-7 D-Ribose 
• 1824-96-0 methyl ribofuranoside 
• 102794-45-6 Carbonic acid allyl ester (2S,3R,4R)-2,3,5-tris-benzyloxy-4-hydroxy-pentyl ester 
• 16838-89-4 2,3,5-tri-O-benzyl-D-ribofuranose 

Downstream Products

• 82064-67-3 1,4-di-O-acetyl-2,3,5-tri-O-benzyl-D-ribinitol 
• 84218-48-4 4-O-acetyl-2,3,5-tri-O-benzyl-D-ribitol 
• 84218-47-3 O-acetyl-1-tri-O-benzyl-2,3,5-D-ribitol 
• 1184727-55-6 1,4-dideoxy-1,4-benzylimino-2,3,5-tri-O-benzyl-L-lyxitol 
• 1431506-41-0 C₂₆H₂₉NO₃ 
• 1431371-90-2 (2S,3S,4S)-5-azido-1,3,4-tri(benzyloxy)-2-iodopentane 
• 1431371-87-7 (2S,3S,4R)-1,3,4-tribenzyloxy-2,5-diiodopentane 
• 14233-62-6 2,3,5-tri-O-benzyl-1-deoxy-D-ribofuranose 
• 1431371-94-6 (2R,3R,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)pyrrolidine hydrochloride 
• 1431371-92-4 C₃₁H₃₇NO₅ 
• 1044757-72-3 2,3,5-tri-O-benzyl-1-O-(4-bromobutyl)-D-ribitol 
• 848649-42-3 2,3,5-tri-O-benzyl-1-O-tert-butyldiphenylsilyl-D-ribitol 
• 112929-26-7 4-O-(3,4,6-tri-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-β-D-glucopyranosyl)-2,3,5-tri-O-benzyl-1-tertiobutyldimethylsilyl-D-ribitol 
• 291758-08-2 2,3,5-tri-O-benzyl-1-O-tert-butyldimethylsilyl-4-O-p-nitrobenzoyl-L-lyxitol 

Relevant academic research and scientific papers

Synthesis, Reactivity, and Stereoselectivity of 4-Thiofuranosides

Thiosugars, sugars that have their endocyclic oxygen substituted for a sulfur atom, have been used as stable bioisosteres of naturally occurring glycans because the thiosugar glycosydic linkage is supposed to be stabilized toward chemical and enzymatic hydrolysis. We have performed an in-depth investigation into the stability and reactivity of furanosyl thiacarbenium ions, by assessing all four diastereoisomeric thiofuranosides experimentally and computationally. We show that all furanosyl thiacarbenium ions react in a 1,2-cis-selective manner with triethylsilane, reminiscent of their oxo counterparts. The computed conformational space occupied by the thiacarbenium ions is strikingly similar to that of the corresponding furanosyl oxycarbenium ions, indicating that the stereoelectronic substituent effects governing the stability of furanosyl oxocarbenium ions and thiacarbenium ions are very similar. While the thio-ribo-furanose appears to be less reactive than its oxo counterpart, the thio-ara-, lyxo-, and xylo-furanosides appear to be more reactive than their oxygen equivalents. These differences are accounted for using the conformational preference of the donors and the carbocation intermediates. The lower reactivity of the thio-ribo furanosides in (Lewis) acid-mediated reactions and the similarity of the thia- and oxocarbenium ions make thio-ribo-furanosides excellent stabilized analogues of the naturally occurring ribo-furanose sugars.

Synthesis and Evaluation of Hybrid Structures Composed of Two Glucosylceramide Synthase Inhibitors

Glucosylceramide metabolism and the enzymes involved have attracted significant interest in medicinal chemistry, because aberrations in the levels of glycolipids that are derived from glucosylceramide are causative in a range of human diseases including lysosomal storage disorders, type2 diabetes, and neurodegenerative diseases. Selective modulation of one of the glycoprocessing enzymes involved in glucosylceramide metabolism - glucosylceramide synthase (GCS), acid glucosylceramidase (GBA1), or neutral glucosylceramidase (GBA2) - is therefore an attractive research objective. In this study we took two established GCS inhibitors, one based on deoxynojirimycin and the other a ceramide analogue, and merged characteristic features to obtain hybrid compounds. The resulting 39-compound library does not contain new GCS inhibitors; however, a potent (200nm) GBA1 inhibitor was identified that has little activity toward GBA2 and might therefore serve as a lead for further biomedical development as a selective GBA1 modulator. Taking the best of both: Two established glucosylceramide synthase (GCS) inhibitors were merged via convergent synthesis to obtain hybrid compounds. Members of this 39-compound library have characteristics of both parent GCS inhibitors. No new GCS inhibitors were established, but a potent (200nm) acid glucosylceramidase (GBA1) inhibitor was identified. This adamantanemethyloxypenanoic acid pyrrolidene-substituted derivative of eliglustat can serve as a lead for further biomedical development of selective GBA1 modulators.

Efficient stereoselective synthesis of oligosaccharides of Streptococcus pneumoniae serotypes 6A and 6B containing multiple 1,2-cis glycosidic linkages

The synthesis of the repeating units of pneumococcal polysaccharide serotypes 6A and 6B and derivatives thereof is described. Application of S-benzoxazolyl and S-thiazolinyl glycosides allowed rapid oligosaccharide assembly and provided complete stereosel

4’-THIONUCLEOSIDES AND OLIGOMERIC COMPOUNDS

The present invention provides modified oligomeric compounds and compositions of oligomeric compounds for use in the RNA interference pathway of gene modulation. The modified oligomeric compounds include siRNA and asRNA having at least one affinity modification.

The stereoselective synthesis of 4'-β-thioribonucleosides via the pummerer reaction

An efficient stereoselective synthesis of 4'-β-thioribonucleosides 14, 15, 27, and 30 using the Pummerer reaction as the key step is described. The Pummerer reaction of 1,4-anhydro-2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopro pyldisiloxane-1,3-di

Facile synthesis of 3'-C-branched 1,5-anhydrohexitol nucleosides

The 3'-β-C-branched anhydrohexitol nucleosides have been conveniently synthesised starting from commercially available D-ribose following the reaction sequence: (i) conversion of protected pentofuranose sugar to the corresponding hexopyranosyl nitrosugar (ii) addition of the conjugate base of nitrosugar to formaldehyde to obtain C-branched nitro sugar (iii) removal of nitro group by n-tributyltin hydride treatment and (iv) Mitsunobu type alkylation to build up the nucleobase.

Synthesis of 3'-C-branched 1',5'-anhydromannitol nucleosides as new antiherpes agents

A series of 3'-β-C-branched anhydromannitol nucleosides were conveniently synthesized starting from commercially available D-ribose. The reaction sequences were: (i) conversion of the protected pentofluranose to the corresponding nitrohexopyranose; (ii) addition of the conjugated base of the nitrosugar to formaldehyde; (iii) removal of the nitro group by n-tributyltin hydride treatment and (iv) Mitsunobu type alkylation to introduce the nucleobase. The conformation of intermediates and final compounds were deduced from NMR analysis. The thymine congener showed potent activity against herpes simplex virus (HSV).

THE RELATIVE STABILITY OF ALLYL ETHER, ALLYLOXYCARBONYL ESTER AND PROP-2 ENYLIDENE ACETAL, PROTECTIVE GROUPS TOWARD IRIDIUM, RHODIUM AND PALLADIUM CATALYSTS.

The deprotection of allyloxycarbonyl derivatives of sugars was realized in the presence of allylether or prop-2-enylidene acetal with Pd(PPh3)4 or RhCl(PPh3)3 as catalyst while PF6 isomerized selectively the allyl ethers.