14125-95-2

Upstream product

• 28072-60-8 3-azido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose 
• 28072-61-9 3-azido-3-deoxy-1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose 
• 55174-91-9 (-)-1,2-O-isopropylidene-5-O-pivaloyl-α-D-xylofuranose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 532-20-7 D-xylofuranose 
• 55174-92-0 1,2-O-isopropylidene-5-O-2,2-dimethylpropanoyl-α-D-erythro-pent-3-ulofuranose 
• 35085-26-8 3-azido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose aldehyde 
• 55174-95-3 1,2-O-isopropylidene-5-O-trimethylacetyl-α-D-erythro-pent-3-ulofuranose oxime 

Downstream Products

• 29881-53-6 3-Acetamino-3-desoxy-1,2-O-isopropyliden-α-D-ribofuranose 
• 1422376-17-7 1,2-O-isopropylidene-3-(4-methoxy)benzylamino-3-deoxy-5-O-tert-butyldimethylsilyl-α-D-ribofuranoside 
• 1422376-18-8 1,2-O-isopropylidene-3-(cyclohexylmethyl)amino-3-deoxy-5-O-tert-butyldimethylsilyl-α-D-ribofuranoside 
• 1422376-20-2 1,2-O-isopropylidene-3-benzylamino-3-deoxy-5-O-n-propyl-α-D-ribofuranoside 
• 1422376-14-4 1,2-O-isopropylidene-3-amino-3-deoxy-5-O-tert-butyldiphenylsilyl-α-D-ribofuranoside 
• 64618-19-5 1,2-O-isopropylidene-3-amino-3-deoxy-5-O-trityl-α-D-ribofuranoside 
• 55174-94-2 3-amino-N-benzyloxycarbonyl-3-deoxy-1,2-O-isopropylidene-α-D-xylofuranose 
• 1361249-84-4 C₂₁H₃₀N₂O₇ 
• 1361250-09-0 C₂₅H₃₆N₂O₈ 
• 1361250-07-8 C₂₆H₃₈N₂O₈ 
• 1361250-05-6 C₂₈H₃₄N₂O₈ 
• 1361250-03-4 C₂₅H₃₆N₂O₈ 
• 1361250-27-2 C₂₅H₃₆N₂O₇S 

Relevant academic research and scientific papers

Synthesis of polyhydroxylated azetidine iminosugars and 3-hydroxy-N-methylazetidine-2-carboxylic acid from d-glucose

The azetidine iminosugars, (2S,3R)-2-((R)-1,2-dihydroxyethyl)azetidin-3-ol 3, (2R,3R)-2-(hydroxymethyl)azetidin-3-ol 4, and (2S,3R)-3-hydroxy-N-methylazetidine-2-carboxylic acid 5 were synthesized from d-glucose derived 3-N-benzyloxycarbonyl-3-deoxy-1,2-O

Sugar-based monodentate phosphoramidite ligands for Cu-catalyzed enantioselective conjugate addition to enones

In this paper we present new, monodentate phosphoramidite ligands based on amines derived from the easy available monosaccharide d-xylose and BINOLs. Ligands were used for copper-catalyzed conjugate addition to acyclic and cyclic enones. The highest enantioselectivity achieved in this study was 77% ee for the conjugate addition to trans-chalcone, which is comparable to the best results published to date for phosphoramidite ligands based on carbohydrate-derived amines.

Modular furanoside phosphite-phosphoroamidites, a readily available ligand library for asymmetric palladium-catalyzed allylic substitution reactions. Origin of enantioselectivity

A library of furanoside phosphite-phosphoroamidite ligands has been synthesized and screened in the palladium-catalyzed allylic substitution reactions of several substrate types. These series of ligands can be prepared efficiently from easily accessible D

SYNTHESIS OF OSELTAMIVIR CONTAINING PHOSPHONATE CONGENERS WITH ANTI-INFLUENZA ACTIVITY

Novel phosphonate compounds are described. The compounds have activity as neuraminidase inhibitors against wild-type and H274Y mutant of H1N1 and H5N1 viruses. The present disclosure also provides an enantioselective synthetic route to known neuraminidase inhibitors oseltamivir and the anti-flu drug Tamiflu, as well as novel phosphonate compounds, via D-xylose. Another efficient and flexible synthesis of Tamiflu and the highly potent neuraminidase inhibitor Tamiphosphor was also achieved in 11 steps and > 20% overall yields from the readily available fermentation product (1S-cis)-3-bromo-3,5- cyclohexadiene-1,2-diol. Most of the reaction intermediates were obtained as crystals without tedious purification procedures. The key transformations include an initial regio- and stereoselective bromoamidation of a bromoarene cis- dihydrodiol, as well as the final palladium-catalyzed carbonylation and phosphonylation.

Synthesis of tamiflu and its phosphonate congeners possessing potent anti-influenza activity

Using d-xylose as an appropriate chiral precursor, we have synthesized active neuraminidase inhibitor oseltamivir, antiflu drug Tamiflu, and novel phosphonate congeners that exhibit even stronger antiflu activities by inhibiting the neuraminidases of the wild-type and H274Y mutant of H1N1 and H5N1 viruses. Molecular modeling of the neuraminidase-phosphonate complex indicates a pertinent binding mode of the phosphonate with three arginine residues in the active site. Discovery of such potent neuraminidase inhibitors will offer an opportunity to the development of new anti-influenza drugs. Copyright

Streptozotocin analogs

New 3-methyl-3-nitrosoureido derivatives of the following amino sugars were prepared as analogs of streptozotocin with the anomeric carbon protected, by nitrosating the methylureas in water with N2 O3 : 3-amino-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose; methyl 3-amino-3-deoxy-β-D-xylopyranoside; methyl 3-amino-3-deoxy-α-D-altropyranoside; methyl 3-amino-3-deoxy-α-D-glucopyranoside; and methyl 3-amino-2,3,6-trideoxy-α-L-lyxohexopyranoside. Tests against murine leukemia L1210 show that the anticancer activity of streptozotocin not only was retained but was enhanced in most of these derivatives.