60134-27-2

Upstream product

• 66108-06-3 Methyl 2,3-anhydro-5-O-(p-toluenesulfonyl)-α-D-ribofuranoside 
• 51255-17-5 1-O-methyl-α-2-deoxy-D-erythro-pentofuranose 
• 98-59-9 p-toluenesulfonyl chloride 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 10437-39-5 methyl 2-deoxy-5-O-(p-toluenesulfonyl)-α,β-D-erythro-pentofuranoside 
• 452-51-7 D-2-deoxyribose 

Relevant academic research and scientific papers

Efficient preparation of 2-nitroimidazole nucleosides as precursors for hypoxia PET tracers

Abstract: 2-Deoxy-D-ribose was converted to α/β-mixtures of methyl 3-O-acetyl- and methyl 3-O-benzoyl-2-deoxy-5-(p-toluenesulfonyl)-D-ribofuranosides. These were reacted with boron trichloride to generate ribofuranosyl chlorides, which afforded precursors for tracers to image tumor hypoxia on substitution with salts of 2-nitroimidazole. The anomeric ratio of the nucleosides was delicately influenced by the reaction conditions. Graphical abstract: [Figure not available: see fulltext.]

Deoxygenated and alkylated furanoses: Thorpe-Ingold effects on tautomeric equilibria and rates of anomerization

2-Deoxy-D-glycero-tetrose, 3-deoxy-DL-glycero-tetrose, 3-deoxy-3,3-di-C-methyl-DL-glycero-tetrose, 3-C-methyl-DL-erythrose, 3-C-methyl-DL-threose, 2-deoxy-5-O-methyl-D-erythro-pentose and 3-deoxy-5-O-methyl-D-erythro-pentose have been prepared, in some cases with 13C-substitution at the anomeric carbon, and characterized by 1H- (300 and 620 MHz) and 13C-n.m.r. (75 MHz) spectroscopy.The proportions of cyclic (α and β furanoses) and acyclic (aldehyde and hydrate) forms were determined in aqueous (2H2O) solution, and ring-opening (kopen) and ring-closing (kclose) rate constants were measured by 1H and 13C saturation-transfer n.m.r. spectroscopy at pH 5.0 (acetate buffer) and 60 deg C.The degree of furanose ring substitution was found to significantly affect both the thermodynamics and kinetics of furanose anomerization.Increased substitution enhances the proportion of cyclic forms in solution by stimulating furanose kclose.In contrast, furanose kopen was less affected by the degree of substitution; however, kinetic studies of 2-deoxyfuranose anomerization implicate furanose ring conformation as a potential determinant of kopen.

Reductive Opening of Sugar Epoxides by Diborane-Borohydride Ion

Carbohydrate epoxides were reduced selectively in the presence of sulfonyl ester, ketal, and acetal groups.Unlike more conventional reagents, such as aluminum hydride, alkoxyaluminum hydrides, and Raney nickel, this reagent permits the presence of a trans-(arylsulfonyl)oxy group adjacent to the epoxide ring.The regioselectivity of the ring-opening reaction appears to be controlled primarily by the steric and polar factors.