Crystal structure of (2H,3S,45,5S)-5-(íerí-butyldimethylsilyl)-3,4-isopropylidene- 2-methylpiperidine-1,3,4,5-tetrol, C15H31NO4Si
Year: 2002
Type: article
Abstract: C15H31NO4SÍ, orthorhombic, C222i (No. 20), a = 6.921(1)Â, b = 22.156(3) Â, c = 25.351(3)Â, V= 3887.1 Â 3 , Z= 8, Rgl(F) = 0.068, wRreffF 2 ) = 0.187, Τ = 293 Κ. Source of materialThe title compound (alternative name: 2-O-terf-butylsilyl-3,4-0isopropylidene-1,5,6-trideoxy-N-hydroxy-1,5-imino-D-mannitol) was prepared as follows.Reduction of an (E/Z) mixture of 2-0fe/7-butyldimethylsilyl-3,4-0-isopropylidene-L-arabino-5-hexenose oxime [1] with sodium cyanoborohydride in methanol at pH = 3 afforded the corresponding primary hydroxylamine which underwent Cope-House cyclization [2-5] in chloroform at room temperature to give the title compound [6,7].This was obtained as a single diastereomer and was purified by column chromatography on silica gel (ethyl acetate / petrol ether 15:85).Crystallization from methanol afforded colourless plates (mp 438-439 Κ, [<z]° = +23 (c = 1.0,CHCI3).
Institution: University of Stuttgart
Language: German
Subfield: Inorganic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $848
OpenAlex ID: W2020786124