Synthesis of compounds

All solvents used were dry, and reactions were carried out under argon atmosphere. The starting materials were purchased from Sigma-Aldrich if not otherwise stated. Heptakis-(6-deoxy-6-mercapto)-beta-CD and hexakis-(6-deoxy-6-mercapto)-beta-CD were purchased from Cyclodextrin-Shop, Netherlands. Care was taken to use a freshly synthesized batch to minimize the presence of disulfides.

Synthesis of sodium undec-10-ene-1-sulfonate

- 11-Bromo-1-undecene (2.122 g, 9.1 mmol) and Na2SO3 (3.061 g, 24.3 mmol) were added into a mixture of MeOH (25 ml) and H2O (45 ml) and refluxed for 18 hours. 

- MeOH was removed under reduced pressure vacuo, and the aqueous layer was washed with Et2O (2 Å~ 50 ml) and dried. 

- The white solid was extracted with hot MeOH and filtered twice, leaving the insoluble Na2SO3 salt on the filter.

- The filtrate was recrystallized from EtOH/H2O mixture (20/1), and the product was collected as white crystalline needles (1.983 g, 85%).

Synthesis of CD1

- Heptakis-(6-deoxy-6-mercapto)-beta-CD (50 mg, 0.040 mmol), sodium undec-10-ene-1-sulfonate (108 mg, 0.421 mmol), and 2,2-dimethoxy-2-

phenylacetophenone (22 mg, 0.084 mmol) were dissolved in DMSO (5 ml). 

- The reaction mixture was placed under ultraviolet (UV) lamp (250 W) and stirred for 18 hours. 

- Crude product was precipitated by the addition of Et2O (45 ml) and collected by centrifugation. 

- The off-white solid was washed by MeOH (45 ml) and EtOH (45 ml) and collected by centrifugation. 

- The product was purified by dialysis against Milli-Q H2O for 3 days, filtered through 0.2-m filter, and collected as a yellow solid (92 mg, 76%).