The first chemical synthesis of a cyclodextrin heteroduplex.
The synthesis of the first heteroduplex of cyclodextrin (CD) 11, i.e., a compound in which the two primary rims of alpha- and beta-CDs are doubly connected, was achieved. The selected strategy involved a Sonogashira coupling of propargylated beta-CD 6 and iodo-alkenyl alpha-CD 4 to singly connect the two CDs. A ring-closing metathesis (RCM) of the heterodimer 9 afforded the second bridge, final deprotection and reductions giving access to 11.
Bistri
Olivia
O
Ecole Normale Supérieure, Département de Chimie, UMR CNRS 8642, 24 rue Lhomond, F-75231 Paris Cedex 05.
Lecourt
Thomas
T
Mallet
Jean-Maurice
JM
Sollogoub
Matthieu
M
Sinaÿ
Pierre
P
D003505:Cyclodextrins / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D003505:Cyclodextrins