Consequences of rigidity and conformational locking in a 4,4-dimethyl-1,3-dioxolane ring system during protection of internal diol.
The presence of an isopropylidene ketal protection of an internal diol in 3,4-O-isopropylidene-D-arabino-1-C-phenyl hexanone locks it in a conformation that prevents its cyclization to a pyranose ring.
Vijayasaradhi
S
S
Department of Chemistry, Indian Institute of Technology, Madras, Chennai 600 036, India.
Aidhen
Indrapal Singh
IS
Varghese
Babu
B
D000475:Alkenes / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D004148:Dioxolanes / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis; D006027:Glycosides / Q000138:chemical synthesis; D006860:Hydrogen Bonding; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared
D000475:Alkenes; D004148:Dioxolanes; D005960:Glucosides; D006027:Glycosides; D007659:Ketones; C013658:propylene; C010962:formal glycol