Title:
METHOD FOR PREPARING N-GLYCOSIDE COMPOUND FROM ALKOXYALLENE COMPOUND USING METAL CATALYST REGIOSELECTIVELY AND STEREOSELECTIVELY
Document Type and Number:
WIPO Patent Application WO/2019/004693
Kind Code:
A1
Abstract:
The present invention relates to a method for preparing an N-glycoside compound from an alkoxyallene compound using a metal catalyst regioselectively and stereoselectively. According to the method for preparing an N-glycoside compound according to the present invention, various N-glycosides can be synthesized from the alkoxyallene compound at a high yield and high optical purity by stereoselectively introducing a carbon-nitrogen bond to a desired position, in the presence of a metal catalyst, regardless of the kind of substituents in the compound.
Inventors:
RHEE YOUNG HO (KR)
KANG SOYEONG (KR)
JANG SEOK HYEON (KR)
LEE JUYEOL (KR)
KIM DONG GIL (KR)
KIM MIJIN (KR)
KANG SOYEONG (KR)
JANG SEOK HYEON (KR)
LEE JUYEOL (KR)
KIM DONG GIL (KR)
KIM MIJIN (KR)
Application Number:
PCT/KR2018/007216
Publication Date:
January 03, 2019
Filing Date:
June 26, 2018
Export Citation:
Assignee:
POSTECH ACAD IND FOUND (KR)
International Classes:
C07H17/02; B01J31/16; C07C43/184; C07H1/00
Other References:
EWING, D. F. ET AL.: "Synthesis of Acyclic Bis-vinyl Pyrimidines: a General Route to d4T via Metathesis", TETRAHEDRON, vol. 59, no. 7, 2003, pages 941 - 945, XP004406407
DONNARD, M. ET AL.: "Ring-rearrangement Metathesis of 3,6-dialkoxy-3,6-dihydro- 2H-pyrans", TETRAHEDRON LETTERS, vol. 49, 2008, pages 1192 - 1195, XP022423202
JI, L. ET AL.: "Palladium-Catalyzed Glycosylation: Novel Synthetic Approach to Diverse N-Heterocyclic Glycosides", ORGANIC LETTERS, vol. 17, no. 6, 2015, pages 1357 - 1360, XP055568854
LI, X. ET AL.: "Glycosylation via Transition-Metal Catalysis: Challenges and Opportunities", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 28, 2016, pages 4724 - 4767, XP055568855
BONCEL, S. ET AL.: "Michael-type Addition as a Convenient Method for Regioselective N-Alkylation of Ambident Uracils", SYNTHESIS, vol. 10, 2010, pages 1573 - 1589, XP055568856
DONNARD, M. ET AL.: "Ring-rearrangement Metathesis of 3,6-dialkoxy-3,6-dihydro- 2H-pyrans", TETRAHEDRON LETTERS, vol. 49, 2008, pages 1192 - 1195, XP022423202
JI, L. ET AL.: "Palladium-Catalyzed Glycosylation: Novel Synthetic Approach to Diverse N-Heterocyclic Glycosides", ORGANIC LETTERS, vol. 17, no. 6, 2015, pages 1357 - 1360, XP055568854
LI, X. ET AL.: "Glycosylation via Transition-Metal Catalysis: Challenges and Opportunities", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 28, 2016, pages 4724 - 4767, XP055568855
BONCEL, S. ET AL.: "Michael-type Addition as a Convenient Method for Regioselective N-Alkylation of Ambident Uracils", SYNTHESIS, vol. 10, 2010, pages 1573 - 1589, XP055568856
Attorney, Agent or Firm:
LEE, Won Hee (KR)
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