An efficient synthesis of cyclodextrin-based carbohydrate cluster compounds.
[formula: see text] The photoaddition of the thiol 2,3,4,6-tetra-O-acetyl-beta-D-1-thioglucopyranose to the allyl ether functions of per-2-allyl-, per-6-allyl-, and per-2,6-diallyl-beta-cyclodextrin derivatives provides a remarkably simple and efficient way for attaching glucopyranose units onto (1) the secondary face, as well as (2) the primary face, of beta-cyclodextrin--not to mention (3) both the primary and secondary faces, simultaneously--in yields of up to 70%.
Fulton
D A
DA
Department of Chemistry and Biochemistry, University of California, Los Angeles 90095-1569, USA.
Stoddart
J F
JF
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D003505:Cyclodextrins / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D002241:Carbohydrates; D003505:Cyclodextrins