TY - JOUR
T1 - Toward fluorinated aminoglycosides
T2 - Structural studies of phenylhydrazine condensation with carbohydrate derivatives
AU - Franconetti, Antonio
AU - Borrachero, Pastora
AU - Gómez-Guillén, Manuel
AU - Cabrera-Escribano, Francisca
PY - 2013
Y1 - 2013
N2 - The reaction of phenylhydrazine with a sugar dialdehyde in water, as a key step for the synthesis of the 3-amino-3-deoxy-d-glucose moiety contained in kanamycin, has been revisited. Structural studies (IR and NMR as well as a simple theoretical model based on energy-minimization calculations and MD calculations) reported herein support the observed stereo- and regioselectivity. Efforts to improve the reproducibility and viability of the process as part of a convenient approach towards fluorinated kanamycin are also now presented.
AB - The reaction of phenylhydrazine with a sugar dialdehyde in water, as a key step for the synthesis of the 3-amino-3-deoxy-d-glucose moiety contained in kanamycin, has been revisited. Structural studies (IR and NMR as well as a simple theoretical model based on energy-minimization calculations and MD calculations) reported herein support the observed stereo- and regioselectivity. Efforts to improve the reproducibility and viability of the process as part of a convenient approach towards fluorinated kanamycin are also now presented.
KW - carbohydrates
KW - condensation
KW - green chemistry
KW - phenylhydrazine
KW - stereo- and regioselectivity
UR - https://www.scopus.com/pages/publications/84872330378
U2 - 10.1055/s-0032-1317783
DO - 10.1055/s-0032-1317783
M3 - Article
AN - SCOPUS:84872330378
SN - 0936-5214
VL - 24
SP - 249
EP - 253
JO - Synlett
JF - Synlett
IS - 2
M1 - ST-2012-D0925-L
ER -