An efficient synthesis of cyclodextrin-based carbohydrate cluster compounds

Organic Letters

Volumn 2, Issue 8, 2000, Pages 1113-1116

  Fulton, David A ^a   Stoddart, J Fraser ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; CYCLODEXTRIN;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMISTRY; CONFORMATION; MASS SPECTROMETRY; MOLECULAR GENETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; CARBOHYDRATES; CYCLODEXTRINS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR SEQUENCE DATA; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 0034689844     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005668x     Document Type: Article

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41. 2, EtOAc/Hexanes] to afford the product. Unreacted thiol 1 can be recovered and reused in subsequent reactions.
42. Reported yields have not been optimized.
43. +.
44. 13C NMR spectra, where the signals corresponding to the CD carbons are weaker and broader than those corresponding to the carbons in the glucose appendages. The reason for this signal broadening is most likely the outcome of a dynamic phenomenon; the glucose appendages start to cause the CD glucose residues to move on a time scale approaching that of the NMR time scale, thus causing the CD signals to broaden.
45. 3OD, 125 MHz): δ 28.7, 32.1, 59.9, 62.6, 63.8, 71.6, 71.9, 72.3, 73.5, 75.2, 80.4, 81.4, 82.7, 83.9, 84.3, 88.1, 100.4.
46. +.
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48. 2O, 125 MHz): δ 26.3, 29.4, 60.0, 60.8, 69.4, 70.4, 71.1, 72.1, 73.5. 79.7, 80.9, 85.2, 99.6.
49. +.
50. 2O, 345 K, 125 MHz): δ 23.7, 26.9, 27.1, 29.9, 30.1, 61.59, 61.66, 69.4, 70.1, 70.3, 70.9, 71.3, 71.6, 72.89, 72.97, 77.82, 77.89, 80.30, 80.35, 81.96, 85.81, 85.88, 100.4.