Preparation of C-(2-deoxyhex/pent-1-enopyranosyl)heterocycles.

@article{Mahmoud1994PreparationOC,
  title={Preparation of C-(2-deoxyhex/pent-1-enopyranosyl)heterocycles.},
  author={Sohir Mahmoud and L{\'a}szl{\'o} Soms{\'a}k and Imre Farkas},
  journal={Carbohydrate research},
  year={1994},
  volume={254},
  pages={91-104}
}
Acetylated 1-cyanoglycals (2,6-anhydro-3-deoxyhept/hex-2-enononitriles) were prepared by direct elimination of acetic acid from the appropriate acetylated 2,6-anhydrohept/hexononitriles with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in aprotic solvents. Heterocyclisation of the cyano group of acetylated 1-cyano-D-galactal with 2-aminothiophenol led to 2-(3,4,6-tri-O-acetyl-2-deoxy-D-lyxo-hex-1-enopyranosyl)benz othiazole. Several 2-(per-O-acetylhexo/pentopyranosyl)benzothiazoles also gave 2-(per… CONTINUE READING