TY - JOUR
T1 - Synthesis of halogenated-4-nitrophenyl 2-deoxy-2-halogeno-pyranosides via n-halogenosuccinimide activated glucal
AU - Inoue, Chieri
AU - Okamoto, Yumi
AU - Vavricka, Christopher J.
AU - Kiyota, Hiromasa
AU - Izumi, Minoru
N1 - Publisher Copyright:
© 2018 Natural Product Incorporation. All Rights Reserved.
PY - 2018/1
Y1 - 2018/1
N2 - Reaction of 3,4,6-tri-O-acetyl-D-glucal with silver 4-nitrophenolate in the presence of N-iodosuccinimide and N-bromosuccinimide produced (2,6-dihalo-4-nitro)phenyl 2-halo-2-deoxy--D-glycopyranosides. Although bromination and iodination of the 4-nitrophenyl group could not be avoided, the resulting (2,6-dihalo-4-nitro)phenylated compounds can be used as substrates or covalent glycosidase inhibitors after deprotection. The stereoselectivity and regioselectivity of the halogenation reactions are described.
AB - Reaction of 3,4,6-tri-O-acetyl-D-glucal with silver 4-nitrophenolate in the presence of N-iodosuccinimide and N-bromosuccinimide produced (2,6-dihalo-4-nitro)phenyl 2-halo-2-deoxy--D-glycopyranosides. Although bromination and iodination of the 4-nitrophenyl group could not be avoided, the resulting (2,6-dihalo-4-nitro)phenylated compounds can be used as substrates or covalent glycosidase inhibitors after deprotection. The stereoselectivity and regioselectivity of the halogenation reactions are described.
KW - 2-Deoxy sugar
KW - 2-Deoxy-2-halogeno-pyranoside
KW - Glucal
KW - N-Halogenosuccinimide
KW - Silver 4-nitrophenolate
UR - https://www.scopus.com/pages/publications/85048512846
UR - https://www.scopus.com/pages/publications/85048512846#tab=citedBy
U2 - 10.1177/1934578x1801300125
DO - 10.1177/1934578x1801300125
M3 - Article
AN - SCOPUS:85048512846
SN - 1934-578X
VL - 13
SP - 85
EP - 87
JO - Natural product communications
JF - Natural product communications
IS - 1
ER -