Mechanism of 2-O→3-O silyl migration in cyclomaltohexaose (α-cyclodextrin)

Tetrahedron Letters

Volumn 44, Issue 26, 2003, Pages 4843-4848

  Teranishi, Katsunori ^a   Ueno, Fumiko ^a  

^a MIE UNIVERSITY   (Japan)

Author keywords

Cyclodextrin; Silyl migration

Indexed keywords

ALPHA CYCLODEXTRIN; SILANE DERIVATIVE;

ALKALINITY; ARTICLE; CHEMICAL REACTION;

PUFFINUS AURICULARIS;

EID: 0038240724     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01149-3     Document Type: Article

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33. 3), 3.20 (1H, dd, J=3.1 and 9.8 Hz, H-2 proton of sulfonylated glucose residue), 3.25 (1H, t, J=9.2 Hz, H-4 proton of sulfonylated glucose residue), 3.25-3.31 (5H, m, H-2 protons of unsulfonylated glucose residues), 3.34-3.41 (5H, m, H-4 protons of unsulfonylated glucose residues), 3.47-3.76 (m), 3.82 (1H, H-5 proton of sulfonylated glucose residue), 4.26-4.32 (2H, m, H-6 protons of sulfonylated glucose residue), 4.66 (1H, d, J=3.1 Hz, H-1 proton of unsulfonylated glucose residue), 4.72 (1H, d, J=3.7 Hz, H-1 proton of sulfonylated glucose residue), 4.77-4.81 (4H, m, H-1 proton of no-sulfonylated glucose residue), 7.42 (2H, d, J=7.9 Hz, ArH), and 7.72 (2H, d, J=7.9 Hz, ArH).
34. 32SSi: C, 47.41; H, 6.50%.
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36. During our studies on the silyl migration, it was shown that the higher the proportion of DMF in the mixture of THF and DMF as the reaction solvent, the lower the efficiency of the silyl migration. Consequently, to attain efficient migration, the proportion of DMF had to be as low as possible, and thus the mixture of THF and DMF was reluctantly used due to the insolubility of 8 for THF.
37. 29SSi: C, 48.89; H, 6.67%.
38. 29SSi: C, 54.76; H, 7.90%.
39. 29SSi: C, 54.76; H, 7.90%.