Palladium-catalyzed C–C coupling: efficient preparation of new 5-thio-β-d-xylopyranosides as oral venous antithrombotic drugs

Scope of the Palladium-Catalyzed Aryl Borylation Utilizing Bis-Boronic Acid

“…This finding does not appear to be unique to this method. Through a thorough literature search of heteroaryl boronates synthesized from B 2 Pin 2 or H-BPin, two trends can be found: either the method reported is purely for one functionalized heteroaryl, − or only a few examples were synthesized under reaction conditions considered under a “general” methods procedure. ,,,,− Also noteworthy is that the heteroaryls examined in this search are among just a handful of heteroaryl borylated products that can be found in the literature, and there is no publication dedicated solely to the Miyaura borylation of heteroaryls using B 2 Pin 2 . Our findings, coupled with the literature results, provide evidence that a general method for the borylation of hetereoaryls remains elusive, and that each substrate or general class of substrates may need to be treated on a case-by-case basis.…”

β-Xylopyranosides: synthesis and applications

“…These molecules were demonstrated to be better substrates for bGalT7 than xylosides. 83,228 Odiparcil™, a b-D-thioxyloside, was compared to warfarin (a chronic oral anti-coagulant). Odiparcil™ exhibits dose-related antithrombotic activity without a dose-related haemorrhagic liability compared with warfarin, which increases the haemorrhagic potential.…”

A Tandem Michael–SN2‐Mediated General Route to Six‐Membered Heterocycles and Carbocycles

“…The importance of six-membered densely functionalized heterocycles [1,2] and carbocycles [3] in natural products and pharmaceuticals has led to outstanding developments in the synthetic strategies for achieving these structures. In particular, polyhydroxylated piperidines, as well as alkyl-and/ or hydroxy-substituted carbocycles, are a common structural component in a large number of naturally occurring and biologically active molecules.…”

“…In particular, polyhydroxylated piperidines, as well as alkyl-and/ or hydroxy-substituted carbocycles, are a common structural component in a large number of naturally occurring and biologically active molecules. [1][2][3] Tandem reactions allow several new bonds to be generated in a one-pot fashion thereby avoiding the isolation of intermediates, minimizing the number of synthetic steps, and eliminating the need for stepwise purification processes. [4] The application of such strategies is therefore highly desirable in synthetic chemistry especially for accessing heterocycles and carbocycles.…”

“…However, the configuration of the ring carbon connected to CH 2 OBn was easily assigned because of the S N 2 nature of the intramolecular cyclization reaction. The structure of 18 was unambiguously established on the basis of an X-ray analysis of its single crystal (Figure 1).…”