Solid‐support synthesis of di‐ and tetramannosylated tetrathymidylic acid

Abstract

Abstract. The easy accessible building units 5-0-(2,3,4,6-tetra-0-benzoyl-a-~mannopyranosyl)penyl 2-cyanoethyl N, N-diisopropylphosphoramidite (9) and 2,2-bis(4,4'-dimethoxytrityloxymethyI)propyl 2-cyanoethyl N, N-diisopropylphosphoramidite (12) were used for the sequential elongation of immobilized tetrametric thymidylic acid according to a DNA synthesis protocol. Ammonolysis of the individual immobilized adducts led to the isolation of the target compounds 1 and 2.

Amphiphilic carbohydrate–phthalocyanine conjugates obtained by glycosylation or by azide–alkyne click reaction

“…Furthermore, the use of ester protecting groups on the C-2 position of the donor will lead to the 1,2-trans glycosides, due to the anchimeric assistance during the glycosylation step. Glycosylation reactions were performed in methylene chloride at 0 1C on the acceptor 3 using respectively 2,3,4,6tetra-O-benzoyl-a-D-glucopyranosyl trichloroacetimidate ( 6), 21 2,3,4,6-tetra-O-benzoyl-a-D-mannopyranosyl trichloroacetimidate (7) 22 8), 23 leading respectively to glycosylated phthalocyanines 9, 10 and 11.…”

“…13 C NMR (CDCl 3 ) : d 137.93, 133.81, 128.78, 127.77, 127.38, 125.04 (aromatics), 70.03, 69.75, 69.74, 69.70, 69. 22,68.22,68.10 (OCH 2 ), 36.75 (SO 2 CH 3 ), 21.74, 28.23, 30.83, 30.84, 30.87 60.10;H,6.94;N,7.28;Found: C,60.07;H,6.94;N,7.25. [2,3,9,10,16,4,7,10tetraoxadodecyl)] phthalocyaninato nickel (5).…”