Abstract
This article describes an efficient synthesis of a potent trehalase inhibitor, 1,1′-N-linked pseudodisaccharide 1 (consisting of two valienamines), in 14 steps with an overall yield of 12% and a first synthesis of 2 (consisting of two 2-epi-valienamines) in 15 steps with an overall yield of 24% from (-)-quinic acid. The synthesis involves a stereospecific palladium-catalyzed coupling reaction between an allylic amine and an allylic chloride as the crucial step. The acetonide blocking groups were shown to be the best hydroxyl protecting groups, compatible with the palladium-catalyzed allylic amination reaction that afforded high yields of the 1,1′-N-linked pseudodisaccharides with a minimum amount of an elimination diene side product.
| Original language | English |
|---|---|
| Pages (from-to) | 15990-15992 |
| Number of pages | 3 |
| Journal | Journal of the American Chemical Society |
| Volume | 126 |
| Issue number | 49 |
| DOIs | |
| Publication status | Published - 2004 Dec 15 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
Cite this
Facile, efficient, and enantiospecific syntheses of 1,1′-N-linked pseudodisaccharides as a new class of glycosidase inhibitors. / Shing, Tony Kung Ming; Kwong, Connie S.K.; Cheung, Aries W.C.; Kok, Stanton H.L.; Yu, Zhifeng; Li, Jianmei; Cheng, Christopher H.K.
In: Journal of the American Chemical Society, Vol. 126, No. 49, 15.12.2004, p. 15990-15992.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Facile, efficient, and enantiospecific syntheses of 1,1′-N-linked pseudodisaccharides as a new class of glycosidase inhibitors
AU - Shing, Tony Kung Ming
AU - Kwong, Connie S.K.
AU - Cheung, Aries W.C.
AU - Kok, Stanton H.L.
AU - Yu, Zhifeng
AU - Li, Jianmei
AU - Cheng, Christopher H.K.
PY - 2004/12/15
Y1 - 2004/12/15
N2 - This article describes an efficient synthesis of a potent trehalase inhibitor, 1,1′-N-linked pseudodisaccharide 1 (consisting of two valienamines), in 14 steps with an overall yield of 12% and a first synthesis of 2 (consisting of two 2-epi-valienamines) in 15 steps with an overall yield of 24% from (-)-quinic acid. The synthesis involves a stereospecific palladium-catalyzed coupling reaction between an allylic amine and an allylic chloride as the crucial step. The acetonide blocking groups were shown to be the best hydroxyl protecting groups, compatible with the palladium-catalyzed allylic amination reaction that afforded high yields of the 1,1′-N-linked pseudodisaccharides with a minimum amount of an elimination diene side product.
AB - This article describes an efficient synthesis of a potent trehalase inhibitor, 1,1′-N-linked pseudodisaccharide 1 (consisting of two valienamines), in 14 steps with an overall yield of 12% and a first synthesis of 2 (consisting of two 2-epi-valienamines) in 15 steps with an overall yield of 24% from (-)-quinic acid. The synthesis involves a stereospecific palladium-catalyzed coupling reaction between an allylic amine and an allylic chloride as the crucial step. The acetonide blocking groups were shown to be the best hydroxyl protecting groups, compatible with the palladium-catalyzed allylic amination reaction that afforded high yields of the 1,1′-N-linked pseudodisaccharides with a minimum amount of an elimination diene side product.
UR - http://www.scopus.com/inward/record.url?scp=10344224590&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=10344224590&partnerID=8YFLogxK
U2 - 10.1021/ja0470158
DO - 10.1021/ja0470158
M3 - Article
C2 - 15584732
AN - SCOPUS:10344224590
VL - 126
SP - 15990
EP - 15992
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 49
ER -