Qualitative evaluation of regioselectivity in the formation of di- and tri-6-O-tritylates of α-cyclodextrin

Keisuke Yoshikiyo,
Yoshihisa Matsui and
Tatsuyuki Yamamoto

Full Research Paper
Published 02 Sep 2015

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1. Graphical Abstract
2. Scheme 1: Tritylates of α-CD examined in the present study and the reaction pathway. Letters A to F represent...
  
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3. Figure 1: UFLC chromatogram of three regioismers of di-6-O-trityl-α-CD with 50% aqueous acetonitrile as an el...
  
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4. Figure 2: UFLC chromatogram of four regioisomers of tri-6-O-trityl-α-CD with an eluent of acetonitrile/methan...
  
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5. Figure 3: A part of ¹³C NMR spectra of di-6-O-trityl-α-CD in DMSO-d₆ at 50 °C a) AD-isomer, b) AC-isomer, and...
  
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6. Scheme 2: A pathway of the conversion of a regioisomer of tri-6-O-trityl-α-CD (ABE isomer) to the correspondi...
  
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7. Figure 4: A part of ¹³C NMR spectra of tri-6-O-trityl-α-CD in DMSO-d₆ at 50 °C. a) ABE-isomer, b) ABD-isomer,...
  
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8. Figure 5: Time-course of the formation of mono- (left ordinate) and di-6-O-tritylates (right ordinate) of α-C...
  
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9. Figure 6: Time-course of the formation of the regioisomers of di-6-O-trityl-α-CD in a reaction of α-CD(Tr)₁ w...
  
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10. Figure 7: Time-course of the formation of the regioisomers of tri-6-O-trityl-α-CD in a reaction of AD-isomer ...
  
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11. Figure 8: Time-course of the formation of the regioisomers of tri-6-O-trityl-α-CD in a reaction of AC-isomer ...
  
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12. Figure 9: Time-course of the formation of the regioisomers of tri-6-O-trityl-α-CD in a reaction of the AB-iso...
  
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13. Figure 10: ¹H NMR spectra of α-CD (a) and the A,D-isomer (b) in DMSO-d₆ at 50 °C.
  
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14. Figure 11: A part of 2D ROESY spectrum of the A,D-isomer in DMSO-d₆ at 50 °C.
  
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