102770-00-3Relevant articles and documents
An orthogonal and reactivity-based one-pot glycosylation strategy for both glycan and nucleoside synthesis: access to TMG-chitotriomycin, lipochitooligosaccharides and capuramycin
He, Haiqing,Xu, Lili,Sun, Roujing,Zhang, Yunqin,Huang, Yingying,Chen, Zixi,Li, Penghua,Yang, Rui,Xiao, Guozhi
, p. 5143 - 5151 (2021)
Both glycans (O-glycosides) and nucleosides (N-glycosides) play important roles in numerous biological processes. Chemical synthesis is a reliable and effective means to solve the attainability issues of these essential biomolecules. However, due to the stereo- and regiochemical issues during glycan assembly, together with problems including the poor solubility and nucleophilicity of nucleobases in nucleoside synthesis, the development of one-pot glycosylation strategies toward efficient synthesis of both glycans and nucleosides remains poor and challenging. Here, we report the first orthogonal and reactivity-based one-pot glycosylation strategy suitable for both glycan and nucleoside synthesis on the basis of glycosylortho-(1-phenylvinyl)benzoates. This one-pot glycosylation strategy not only inherits the advantages including no aglycon transfers, no undesired interference of departing species, and no unpleasant odors associated with the previously developed orthogonal one-pot glycosylation strategy based on glycosylortho-alkynylbenzoates, but also highly expands the scope (glycans and nucleosides) and increases the number of leaving groups that could be employed for the multistep one-pot synthesis (up to the formation of four different glycosidic bonds). In particular, the current one-pot glycosylation strategy is successfully applied to the total synthesis of a promising tuberculosis drug lead capuramycin and the divergent and formal synthesis of TMG-chitotriomycin with potent and specific inhibition activities toward β-N-acetylglucosaminidases and important endosymbiotic lipochitooligosaccharides including the Nod factor and the Myc factor, which represents one of the most efficient and straightforward synthetic routes toward these biologically salient molecules.
IMPROVED SYNTHESIS OF CAPURAMYCIN AND ITS ANALOGUES
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, (2015/03/13)
Provided herein are compounds of Formula I, Formula II, and Formula X, which are useful for the treatment of infectious diseases. Also provided herein are processes for preparing 1-[5-0-[4,6-Dideoxy-6-oxo-6-[[[(3S)-hexahydro-2-oxo-1H-azepine]-3-y1]amino]-Pβ-L-erythro-4- hexenopyranosyl]-3-0-methyl 6-deoxy-6-amino-α-L-talofuranuronosyl]-1,2,3,4-tetrahydro-2,4- dioxopyrimidine (capuramycin), analogues thereof, and intermediates useful therefore. Also provided herein are III, IIIa, and IX, which are useful in the process for preparing capuramycin and/or a certain compound of Formula I.
Improved synthesis of capuramycin and its analogues
Wang, Yong,Siricilla, Shajila,Aleiwi, Bilal A.,Kurosu, Michio
, p. 13847 - 13858 (2013/10/22)
Capuramycin and its congeners are considered to be important lead molecules for the development of a new drug for multidrug-resistant (MDR) Mycobacterium tuberculosis infections. Extensive structure-activity relationship studies of capuramycin to improve the efficacy have been limited because of difficulties in selectively chemically modifying the desired position(s) of the natural product with biologically interesting functional groups. We have developed efficient syntheses of capuramycin and its analogues by using new protecting groups, derived from the chiral (chloro-4-methoxyphenyl)(chlorophenyl)methanols, for the uridine ureido nitrogen and primary alcohol. The chiral nonracemic (2,6-dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)methanol derivative is a useful reagent to resolve rac-3-amino-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin- 2-one, the (S)-configuration isomer of which plays a significant role in improving the mycobactericidal activity of capuramycin. Battling TB: Capuramycin and its congeners (see scheme) are considered to be important lead molecules for the development of a new drug for multidrug-resistant Mycobacterium tuberculosis infections. Efficient synthesis of capuramycin and its analogues by using new protecting groups for the uridine ureido nitrogen and primary alcohol was accomplished. Copyright
Concise synthesis of capuramycin
Kurosu, Michio,Li, Kai,Crick, Dean C.
supporting information; experimental part, p. 2393 - 2396 (2009/10/23)
A concise total synthesis of capuramycin (1), a promising preclinical TB drug lead, is achieved by high-yield formations of the cyanohydrin 5a and 4″,5″-glycal derivative 12. Capuramycin can be synthesized in eight steps from the uridine building block 5a with 30% overall yield. The synthetic intermediates reported here are useful for generation of analogs to improve pharmacokinetic properties of capuramycin.
Synthesis of capuramycin
Knapp,Nandan
, p. 281 - 283 (2007/10/02)
The structure of capuramycin (1) is confirmed by an efficient synthesis that features glycosylation with a D-manno-pyranuronate donor 15 at the hindered C-5' hydroxyl of L-talo-uridine 10.
