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Synthesis of Unprotected O-Glycosyl Trichloroacetimidates Structure Assignment and New Results

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1994

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Haeckel, Roland
Troll, Carsten

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http://nbn-resolving.de/urn:nbn:de:bsz:352-233883
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https://doi.org/10.1055/s-1994-22748
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Synlett. 1994, 1994(01), pp. 84-86. ISSN 0936-5214. eISSN 1437-2096. Available under: doi: 10.1055/s-1994-22748

Zusammenfassung

X-Ray analysis of crystals obtained via base-catalyzed O-deacetylation of O-glucosyl-trichloroacetimidate 1a revealed formation of amide acetal 3a. The previously assigned unprotected O-glucosyl-trichloroacetimidate structure 2a (ref. 2) was not found in the 1H-NMR as possible equilibrium product. Yet, acid-catalyzed glycosylation with amide acetal 3a follows the trichloroacetimidate route and not the orthoester route. 3,4,6-Tri-O-benzyl-D-glucose (11) gave with trichloroacetonitrile in the presence of DBU as the base amide acetal 12; however, in the presence of K2CO3 as the base 2-O-unprotected trichloroacetimidate 13 (α/β-mixture) was obtained, thus exhibiting that O-unprotected O-glycosyl-trichloroacetimidates can be obtained via direct anomeric O-trichloroacetimidoylation without subsequent 2-hydroxy group attack leading to amidacetals.

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540 Chemie

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ISO 690HAECKEL, Roland, Carsten TROLL, Helmut FISCHER, Richard R. SCHMIDT, 1994. Synthesis of Unprotected O-Glycosyl Trichloroacetimidates Structure Assignment and New Results. In: Synlett. 1994, 1994(01), pp. 84-86. ISSN 0936-5214. eISSN 1437-2096. Available under: doi: 10.1055/s-1994-22748
BibTex
@article{Haeckel1994Synth-23388,
  year={1994},
  doi={10.1055/s-1994-22748},
  title={Synthesis of Unprotected O-Glycosyl Trichloroacetimidates Structure Assignment and New Results},
  number={01},
  volume={1994},
  issn={0936-5214},
  journal={Synlett},
  pages={84--86},
  author={Haeckel, Roland and Troll, Carsten and Fischer, Helmut and Schmidt, Richard R.}
}
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