Organotitanium-induced stereoselective alkylative endo-cleavage of benzyl pentopyranosides

Roger Olsson, Pontus Rundström, Björn Persson, Torbjörn Frejd

Forskningsoutput: TidskriftsbidragArtikel i vetenskaplig tidskriftPeer review

Sammanfattning

The results presented are the first examples where organotitanium reagents induced alkylative endo-cleavage of carbohydrates. The best conditions for the alkylative transfer of a methyl group to benzyl 2-deoxy- 2-C-methyl-4-O-(tert-butyldimethylsilyl)-α-D-arabinopyranoside (1) were the application of one equivalent of AlMe3 followed by four equivalents of MeTiCl3 generated by mixing TiCl4 and ZnMe2 in a ratio 2:1, or, alternatively, treatment of I with two equivalents of 1:1 Me2TiCl2-ZnMe2. Both the yields and diastereoselectivities were comparable with those of the reaction with AlMe3 but the titanium reagents were more reactive and could be applied at much lower temperatures than the aluminium reagent.

Originalspråkengelska
Sidor (från-till)13-18
TidskriftCarbohydrate Research
Volym307
Nummer1-2
DOI
StatusPublished - 1998 feb.

Ämnesklassifikation (UKÄ)

  • Läkemedelskemi

Fingeravtryck

Utforska forskningsämnen för ”Organotitanium-induced stereoselective alkylative endo-cleavage of benzyl pentopyranosides”. Tillsammans bildar de ett unikt fingeravtryck.

Citera det här