Slide 10 of 21
Notes:
Start with Native b-cyclodextrin
Protect the primary hydroxyls with tert-butyl dimethyl silyl chloride
Then methylate the secondary hydroxyl groups along the bottom of the protected cyclodextrin
After the secondary hydroxyls were methylated, the primary hydroxyl groups were deprotected.
Carboxymethylation was accomplished with the addition of ethyldiazoacetate
Removal of the ethyl group and subsequent protonation were accomplished in a strong base followed by ion exchange chromatography.
NMR was used to characterize each intermediate as well as the final product.
Column chromatography (on silica gel) was used to purify each intermediate (except number 2)
Overall yield was about 38%.
