10.1021/ol0491890.s002
Ke-Gang Liu
Ke-Gang
Liu
Shi Yan
Shi
Yan
Yu-Lin Wu
Yu-Lin
Wu
Zhu-Jun Yao
Zhu-Jun
Yao
Synthesis of
4-Azido-4-deoxy-Neu5,7,8,9Ac<sub>4</sub>2en1Me. A
Key Intermediate for the Synthesis of
GG167 from d-Glucono-δ-lactone
American Chemical Society
2004
Key Intermediate
Azido
imine
diastereoselective allyllation
1Me
acid
chemoselective oxidations
regioselective
Relenza
neuraminidase inhibitor GG 167
ester
GG 167
synthesis
methyl
Zanamivir
material
acetyl
acetamido
Stereoselective
vicinal diols
Synthesi
aziridine
2004-06-24 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Synthesis_of_4_Azido_4_deoxy_Neu5_7_8_9Ac_sub_4_sub_2en1Me_A_Key_Intermediate_for_the_Synthesis_of_GG167_from_d_Glucono_lactone/3334717
Stereoselective synthesis of 5-acetamido-7,8,9-tri-<i>O</i>-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-d-glycero-d-galacto-non-2-enonic acid methyl ester,
an advanced key intermediate for the synthesis of neuraminidase inhibitor GG167 (Zanamivir, Relenza), was accomplished using d-glucono-δ-lactone as starting material. A highly diastereoselective allyllation of an imine intermediate, a regioselective azide-opening of an aziridine,
and chemoselective oxidations of vicinal diols served successfully as key steps.