Chemical synthesis of cyclodextrins by using intramolecular glycosylation.
An efficient synthesis of cyclodextrins (CDs) by using the intramolecular glycosylation is demonstrated. alpha-CD, an alpha(1-->4)linked hexaglucoside, was prepared via a block condensation of three maltose units. A modified key maltose intermediate as a precursor to both glycosyl donor and acceptor components was prepared in 6 steps starting from maltose. All the glycosylation for chain elongation and cyclization of saccharides was carried out after tethering the donor to the acceptor by the phthaloyl bridge to give the desired saccharides in good yields with complete alpha-selectivity. delta-CD composed of 9 glucose units was synthesized by the same manner from three maltotriose units.
Wakao
Masahiro
M
Department of Chemistry, Graduate School of Science, Osaka University, Machikaneyama 1-1, Toyonaka, Osaka 560-0043, Japan.
Fukase
Koichi
K
Kusumoto
Shoichi
S
D003505:Cyclodextrins / Q000138:chemical synthesis*; D005947:Glucose / Q000737:chemistry; D006031:Glycosylation; D008320:Maltose / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D003505:Cyclodextrins; D008320:Maltose; D005947:Glucose