Vorbriiggen coupling

Some 5 -0-(a-aminoacyl) derivatives of ribavirin have been made using DCC coupling.3l2 The 5 -0-sulfamoylribose derivative 229 was used in modified Vorbriiggen couplings with various bases to make a range of S -O-sulfamoyl nucleosides related to the herbicidal natural product lead compound, 2-chloroadenosine S -sulphamate, but most of the analogues were toxic in a mammalian cell line.313... 

An important reaction is used by many today to prepare many nucleosides. The Vorbriiggen glycosylation reaction (H. Vorbriiggen, Germany) couples a highly protected heterocycle, such as 116, protected as the trimethysilyloxy derivative. Reaction of 116 and tetraacetyl ribofuranose 117 in the presence... 

As regards synthetic methods, a full account has been given of the use of methyl 2,3,5-tri-O -benzoyl- D-ribofuranosyl carbonate in condensations with silylated heterocycles in the presence of silver salts and diphenyltin sulfide (see Vol. 27, p. 242), and similar condensatimis can also occur with high selectivity in the presence of tin(II) chloride in acetonitrile. Thp derivatives of heterocycles have been used in Vorbriiggen-type couplings, P-D-ribofuranosyl derivatives of purines, pyrimidines, imidazoles and pyrazoles being made in this way. ... 

Previously reported intermediates (Vol.27, p.253-4) have been converted into other nucleoside analogues with two-carbon chains at C-2, such as the selectively-protected triol 87, prepared by reduction of the lactone 86. 2 -C-Methyl ribonucleosides have been made by Vorbriiggen-type coupling of the appropriate base to a sugar unit (see Chapter 14). 

The use of 2-N-acetyl-6-0-diphenylcarbamoylguanine in Vorbriiggen - type couplings ensures the formation of 9-glycosyl guanine nucleo-... 

The aziridinonucleosides 47 (B Ura, Thy) have been made by Vorbriiggen-type coupling of the sugar with silylated heterocycles. ... 

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