- Total synthesis of (+)-valienamine and (-)-1-epi-valienamine via a highly diastereoselective allylic amination of cyclic polybenzyl ether using chlorosulfonyl isocyanate
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The total synthesis of (+)-valienamine and (-)-1-epi-valienamine was concisely accomplished from readily available d-glucose via a highly diastereoselective amination of chiral benzylic ether using chlorosulfonyl isocyanate, intramolecular olefin metathesis, and diastereoselective reduction of cyclic enone using l-Selectride as the key steps.
- Li, Qing Ri,Kim, Seung In,Park, Sook Jin,Yang, Hye Ran,Baek, A Reum,Kim, In Su,Jung, Young Hoon
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p. 10384 - 10390
(2013/11/19)
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- FAMILY OF ARYL, HETEROARYL, O-ARYL AND O-HETEROARYL CARBASUGARS
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The present invention relates to a compound of the following formula (I): as well as its process of preparation, pharmaceutical and cosmetics composition comprising it and use thereof, notably as an inhibitor of the sodium-dependent glucose co-transporter, such as SGLTl, SGLT2 and SGLT3, in particular in the treatment or prevention of diabetes, and more particularly type-II diabetes, diabetes-related complications, such as arthritis of the lower extremities, cardiac infarction, renal insufficiency, neuropathy or blindness, hyperglycemia, hyperinsulinemia, obesity, hypertriglyceridemia, X syndrome and arteriosclerosis, as well as for its use as an anticancer, anti-infective, anti-viral, anti-thrombotic or anti- inflammatory drug, or for lightening, bleaching, depigmenting the skin, removing blemishes from the skin, particularly age spots and freckles, or preventing pigmentation of the skin.
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Page/Page column 77
(2012/12/13)
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- Nucleotidylation of unsaturated carbasugar in validamycin biosynthesis
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Validamycin A is a member of microbial-derived C7N-aminocyclitol family of natural products that is widely used as crop protectant and the precursor of the antidiabetic drug voglibose. Its biosynthetic gene clusters have been identified in seve
- Yang, Jongtae,Xu, Hui,Zhang, Yirong,Bai, Linquan,Deng, Zixin,Mahmud, Taifo
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scheme or table
p. 438 - 449
(2011/03/17)
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- Studies on the synthesis of valienamine and 1-epi-valienamine starting from d-glucose or l-sorbose
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Two synthetic routes to a carbocyclic precursor to valienamine are reported, starting from either d-glucose or l-sorbose and using ring-closing metathesis as a key step. A low-yielding synthesis of 1-epi-valienamine is reported. Results from an abortive third possible route to valienamine based on an early introduction of nitrogen are discussed.
- Cumpstey, Ian,Gehrke, Sebastian,Erfan, Sayeh,Cribiu, Riccardo
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p. 1675 - 1692
(2008/12/21)
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- Formal synthesis of valienamine using ring-closing metathesis
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(1R,2S,3S,4R)-2,3,4-Tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3, 4-tetrol, a precursor of the α-glucosidase inhibitor, valienamine, was synthesised in eight steps from tetrabenzyl glucose. The key steps were the selective protection of an open-c
- Cumpstey, Ian
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p. 6257 - 6259
(2007/10/03)
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