TY - JOUR
T1 - Synthesis of the 2,3,4-triacetyl-1,6-dideoxy-L-mannose and tetracetyl-3,6-dideoxy-L-mannitol and the study of the reaction mechanism by molecular modeling
AU - Bañuelos-Hernández, A. E.
AU - Mendoza-Espinoza, J. A.
PY - 2014/7
Y1 - 2014/7
N2 - The carbohydrate compounds have interesting stereochemical properties and can be used as chiral building blocks in the production of more complex derivatives. L-Rhamnose has been reported to participate in the synthesis of cytotoxic α-pyrones owing to the stereochemistry of the hydroxy groups. To study the conformational properties of acetyl derivatives of L-rhamnose, it was tosylated with the subsequent reduction and acetylation. These series of reactions produced an interesting mixture of poly-acetylated compounds. The mixture was separated by HPLC, characterized by 1D and 2D NMR techniques and compared with models obtained on DFT/B3LYP/DGDZVP theory level of calculation, taking into account the effect of pyridine as solvent in the transformation of this carbohydrate. The results show a mixture of three pyranoside products with tosyl group in positions 2, 3, and 4. These latter compounds after reduction with aluminum hydride and acetylation yielded two main products, one triacetate pyranoside and an open-chain mannositol tretraacetate.
AB - The carbohydrate compounds have interesting stereochemical properties and can be used as chiral building blocks in the production of more complex derivatives. L-Rhamnose has been reported to participate in the synthesis of cytotoxic α-pyrones owing to the stereochemistry of the hydroxy groups. To study the conformational properties of acetyl derivatives of L-rhamnose, it was tosylated with the subsequent reduction and acetylation. These series of reactions produced an interesting mixture of poly-acetylated compounds. The mixture was separated by HPLC, characterized by 1D and 2D NMR techniques and compared with models obtained on DFT/B3LYP/DGDZVP theory level of calculation, taking into account the effect of pyridine as solvent in the transformation of this carbohydrate. The results show a mixture of three pyranoside products with tosyl group in positions 2, 3, and 4. These latter compounds after reduction with aluminum hydride and acetylation yielded two main products, one triacetate pyranoside and an open-chain mannositol tretraacetate.
KW - L-rhamnose
KW - conformational analysis
KW - molecular modeling
KW - reaction mechanism
UR - http://www.scopus.com/inward/record.url?scp=84906246774&partnerID=8YFLogxK
U2 - 10.1134/S1070363214070342
DO - 10.1134/S1070363214070342
M3 - Artículo
AN - SCOPUS:84906246774
SN - 1070-3632
VL - 84
SP - 1450
EP - 1457
JO - Russian Journal of General Chemistry
JF - Russian Journal of General Chemistry
IS - 7
ER -