OCTAKIS-6-IODO-6-DEOXY-GAMMA-CYCLODEXTRIN synthesis

Yield:168296-33-1 92%

Reaction Conditions:

with tetraethylammonium iodide;4-pyrrolidin-1-ylpyridine;ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate in N,N-dimethyl-formamide at 20;regioselective reaction;

Steps:

Per(6-deoxy-6-halo)cyclodextrins 2; General Procedure

General procedure: To a solution of freshly dried cyclodextrin 1 (2 mmol) in anhydrous DMF (40 mL) were added XtalFluor-E (2 equiv per glucose unit),4-(1-pyrrolidino)pyridine (1 equiv per glucose unit) and an anhydrous tetraethylammonium halide (2 equiv per glucose unit) with stirring at r.t. After the reaction was complete, as monitored by TLC, DMF was removed under reduced pressure and the resulting residue was poured into sat. Na₂CO₃ solution (50 mL); the reaction mixture was stirred for another 1 h. Addition of cold acetone (200mL) gave a precipitate which was collected by filtration and exhaustively washed with H₂O and acetone to afford 2 as a white or pale brown solid.

References:

Liu, Xiaofeng;Cheng, Sen;Wang, Xiaolei;Xue, Weihua [Synthesis,2013,vol. 45,# 22,art. no. SS-2013-H0456-OP,p. 3103 - 3105]