Some amino sugars structurally related to 6-deoxymannojirimycin precursors prepared from methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose and methyl 2,3-O-isopropylidene-alpha-D-lyxo-pentodialdo-1,4-furanoside.
Methyl (5S)-5-C-amino-5-cyano-5-deoxy-2,3-O-isopropylidene-alpha-D-lyxofuranoside has been synthesised from methyl 2,3-O-isopropylidene-alpha-D-lyxo-pentodialdo-1,4-furanoside, applying the Strecker synthesis. Analogously, methyl (5S) and (5R)-5-C-amino-5-cyano-5,6-dideoxy-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosides were prepared from methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose. The 5-S configuration was unambiguously determined by single-crystal X-ray diffraction analysis of corresponding N-acetyl derivatives. Conformations of five-membered rings are discussed. The conversion of N-acetylated amino nitriles to N-acetylamino acid ethyl ester and amide, respectively, is also described.
Micová
Júlia
J
Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-84238 Bratislava, Slovak Republic.
Steiner
Bohumil
B
Koós
Miroslav
M
Langer
Vratislav
V
Durík
Marián
M
Gyepesová
Dalma
D
Smrcok
L'ubomír
L
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives; D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D018360:Crystallography, X-Ray; D004187:Disaccharides / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D015394:Molecular Structure; D009570:Nitriles; D010429:Pentoses / Q000737:chemistry*; D012210:Rhamnose / Q000031:analogs & derivatives*
C435774:6-deoxymannojirimycin; D000606:Amino Sugars; D004187:Disaccharides; D009570:Nitriles; D010429:Pentoses; C476422:methyl 2,3-O-isopropylidene-pentodialdo-1,4-furanoside; C476421:methyl 6-deoxy-2,3-O-isopropylidene-hexofuranosid-5-ulose; D017485:1-Deoxynojirimycin; D012210:Rhamnose