23885-38-3

Upstream product

• 26775-14-4 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 286011-06-1 1,2:5,6-di-O-isopropylidene-α-D-galactofuranose 
• 35777-79-8 5,6-di-O-benzoyl-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose 
• 14686-88-5 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 22331-19-7 3-O-benzyl-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose 
• 65434-49-3 3-O-benzyl-1,2-O-isopropylidene-α-D-galactofuranose 
• 77-76-9 2,2-dimethoxy-propane 
• 4205-23-6 D-gulose 
• 2595-05-3 Diacetone D-glucose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 

Downstream Products

• 65877-63-6 3-O-benzyl-D-glucopyranose 
• 142929-66-6 methyl 3-O-benzyl-β-D-gulofuranoside 
• 143005-10-1 methyl 3-O-benzyl-β-D-gulopyranoside 
• 143005-11-2 methyl 3-O-benzyl-α-D-gulopyranoside 
• 142946-29-0 6,7-di-O-benzylbengamide E 
• 142946-34-7 cis-6,7-di-O-benzylbengamide E 
• 143005-12-3 methyl 3-O-benzyl-4,6-O-benzylidene-β-D-gulopyranoside 
• 142929-68-8 Acetic acid 2-benzenesulfonyl-1-((2S,3R,4R,5R,6R)-3,4-bis-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-yl)-3-methyl-butyl ester 
• 142929-70-2 methyl 3,4-di-O-benzyl-6,7-didehydro-6,7-dideoxy-7-C-isopropyl-2-O-methyl-β-D-guloheptopyranoside 
• 142929-71-3 3,4-di-O-benzyl-6,7-didehydro-6,7-dideoxy-7-C-isopropyl-2-O-methyl-β-D-gulono-1,5-lactone 
• 143058-64-4 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-β-D-gulopyranoside 
• 1053613-62-9 (2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-carbaldehyde 
• 142929-67-7 methyl 3,4-di-O-benzyl-2-O-methyl-β-D-gulopyranoside 
• 237749-86-9 (2R,3S,4S)-4-Benzyloxy-4-(1H-imidazol-4-yl)-butane-1,2,3-triol 

Relevant academic research and scientific papers

Titanocene dihalides and ferrocenes bearing a pendant α-d- xylofuranos-5-yl or α-d-ribofuranos-5-yl moiety. synthesis, characterization, and cytotoxic activity

Titanocene dichlorides of general formula [(η5-C 5H5)(η5-C5H4R) TiCl2] (where R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl-α- d-xylofuranos-5-yl (Xylf) (8a); R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl- α-d-ribofuranos-5-yl (Ribf) (8b)) and [(η5-C 5H4R)2TiCl2] (R = Xylf (9a); R = Ribf (9b)) were prepared by reaction of the corresponding lithium cyclopentadienides 7a,b with an equimolar amount of [(η5-C 5H5)TiCl3] or a 0.5 mol amount of [TiCl 4(THF)2]. Titanocene difluorides of the general formula [(η5-C5H4R1)(η5- C5H4R2)TiF2] (R1 = H and R2 = Ribf (10); R1 = R2 = Xylf (11a); R 1 = R2 = Ribf (11b)) were obtained by fluorination of the corresponding titanocene dichlorides 8b and 9 with the fluorinating agent {2-(CH2NMe2)C6H4-κC,N}(n-Bu) 2SnF in high yields. Alternatively, complexes 11 were prepared in a straightforward way by direct reaction of [TiF4(THF)2] with 2 equiv of the corresponding lithium cyclopentadienide 7a,b. Ferrocene complexes [(η5-C5H4R)2Fe] (R = Xylf (12a); R = Ribf (12b)) were synthesized by metathesis of 2 equiv of lithium cyclopentadienide 7a,b and 1 equiv of anhydrous FeCl2. Deprotection of the benzyl group in ferrocenes 12 proceeded cleanly by a catalytic hydrogenation on Pd/C and afforded the ferrocene diols [(η5- C5H4R)2Fe] (R = 5-deoxy-1,2-di-O- isopropylidene-α-d-xylofuranos-5-yl (Xylf-OH) (14a); R = 5-deoxy-1,2-di-O-isopropylidene-α-d-ribofuranos-5-yl (Ribf-OH) (14b)). A scaled up benzyl deprotection with Et3SiH as a hydrogen source led to the replacement of only one benzyl group, which gave the ferrocene alcohol [(η5-C5H4R1)(η5- C5H4R2)Fe] (R1 = Xylf and R 2 = Xylf-OH (13)). The prepared complexes were characterized by elemental analysis, melting point determination, NMR, IR, and ESI-MS, and the molecular structure of 9b was determined by X-ray diffraction analysis. The cytotoxic activity of complexes 8-14 against A2780 and A2780cis cancer cells was evaluated by MTT tests. Titanocene difluorides 10 and 11 and ferrocene diol 14a showed cytotoxicity against A2780 cells in the medium to low micromolar range, while the most active species, 11b, displayed about 40% higher cytotoxicity against A2780cis in comparison to a cisplatin standard.

The Glc2Man2-fragment of the N-glycan precursor - A novel ligand for the glycan-binding protein malectin?

The Glcα(1→3)Glcα(1→3)Manα(1→2)Man tetrasaccharide (Glc2Man2-fragment), a substructure of the natural N-glycan precursor, was synthesized. The interaction of this fragment with the protein malectin, a carbohydrate binding protein localized in the endoplasmatic reticulum, was investigated by 1H15N HSQC experiments and isothermal calorimetry. The chemical shift perturbations of nuclei in the protein's backbone caused by the binding of the Glc 2Man2-fragment to malectin suggest a binding mode like the known ligand nigerose. The Royal Society of Chemistry 2010.

Stereoisomeric imidazolo-pentoses - Synthesis, chiroptical properties, and evaluation as glycosidase inhibitors

The syntheses of all four imidazolo-piperidino-pentoses in the L-series ent-2 to ent-5, and of three out of the four possible stereomers in the D-series 3, 4, and 5, are reported. The linear imidazolo sugar precursors were prepared, either by double condensation of formamidine with protected aldohexoses, or by nucleophilic addition of a lithiated imidazole derivative to protected aldotetroses. Cyclisation of these linear imidazolo-carbohydrates was performed by intramolecular SN2 reactions. These were followed by deprotection to the target molecules. The four pairs of opposite enantiomers showed pronounced mirror-image-type Cotton effects in their CD spectra. All stereomers of the D-series show a negative rotatory power ([α]D), while the stereomers of the L-series show a positive one. None of the eight imidazolo sugars inhibited the replication of HIV-1. Some of them proved to be rather selective but only moderately potent inhibitors of α-glycosidases, as determined by Michaelis-Menten kinetics.

Improved double epimerisation of (D)-glucose into (D)-gulose and the synthesis of (D)-xylo-imidazolopiperidinose

Rhodium/alumina catalysed cis-hydrogenation of the known enol-acetate 7 proceeded quantitatively and with complete stereoselectivity leading to the D-gulose derivative 8. Several reaction steps permitted transformation of 8 into the target D-xylo-imidazolopiperidinose ent-4 molecule, i.e, the enantiomer of the already known imidazolo-sugar 4.

Ortho Ester Claisen Rearrangements of Three 3-C-(Hydroxymethyl)methylene Derivatives of Hexofuranose: Stereoselective Introduction of a Quaternary Center on C-3 of D-ribo-, L-lyxo-, and D-arabino-Hexofuranoses

Ortho ester Claisen rearrangements of (E)-3-deoxy-3-C--1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranose (3-E), -β-L-lyxo-hexafuranose (12-E), and -β-D-arabino-hexofuranose (33-E) proceeded with high stereoselectivity to provide the rearranged products 13, 15, and 34, respectively, in acceptable yields.The rearrangements of the corresponding Z isomers 3-Z, 12-Z, and 33-Z were also investigated.The stereochemistries of the newly introduced quaternary center on C-3 of compounds 13, 15, and 34 were established unambiguouosly by chemical modifications of each rearranged product.