C-Arylglycoside, synthesis

Kometani, T, Kondo, H, Fujimori, Y, Boron trifluoride-catalyzed rearrangement of 2-aryloxyte-trahydropyrans a new entry to C-arylglycosidation, Synthesis, 1005-1007, 1988. 

Table 24 Synthesis of C-arylglycosides with triarylindium. Reproduced with permission from Elsevier...

Schmidt, R R, Frick, W, Haag-Zeino, B, Apparao, S, De-novo synthesis of carbohydrates and related natural products. Part 28. C-arylglycosides and 3-deoxy-2-glyculosonates via inverse type hetero-Diels-Alder reaction, Tetrahedron Lett., 28, 4045 -4048, 1987. 

C-Arylglycosides possess a stable C-C glycosidic linkage and exhibit a broad range of useful antitumor, antifungal and antibiotic properties. S.R. Pulley et al. developed a novel method for the synthesis of this important class of compounds by using the Dotz benzannuiation reaction between alkynyl glycosides and alkoxy phenyl chromium... 

So far, the only examples of O-C migrations have applied to pyranose sugars or derivatives thereof. However, it should be noted that such reactions are applicable to furanose sugars. One particular example, reported by Matsumoto, et al.,101 was used in the total synthesis of gilvocarcin M. The specific reaction, shown in Scheme 2.4.25, utilized the acetoxy activated furanoside shown. Treating this compound with the phenol and using the hafnocene dichloride-silver perchlorate complex as the Lewis acid, the desired C-arylglycoside was obtained in 87% yield with the a anomer favored in a ratio of 8 1. 

B.iv.c. Stereospecific Synthesis of C-Arylglycosides. The Pd- or Ni-catalyzed reaction of a-O-A -glycopyranoside (1) with arylmagnesium bromides has provided a- or /3-C-aryl-A -glycopyranosides, respectively, exhibiting 100% stereospecihcity in each case " (Scheme 19). A related stndy with aryltins and arylsilicates has also been pnblished.t ... 

Cristau H-J, Monbrun J, Schleiss J, Virieux D, Pirat J-L (2005) First synthesis of F-aryl-phosphinosugars, organophosphorus analogues of C-arylglycosides. Tetrahedron Lett 46 3741-3744... 

Parker, K. A. and Georges, A. T. 2000. Reductive aromatization of quinols Synthesis of the C-arylglycoside nucleus of the papulacandins and chaetiacandin. Org. Lett. 2 497 99. 

Scheme 5). The glycosidation is also referred to in Chapter 3, as is the synthesis of the 8-C-arylglycoside nucleus of cl aetia-candin. 

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