80040-79-5Relevant academic research and scientific papers
Iterative Synthesis of 2-Deoxyoligosaccharides Enabled by Stereoselective Visible-Light-Promoted Glycosylation
Guo, Zhen-Yan,Liu, Kai-Meng,Liu, Meng,Liu, Miao,Qin, Xian-Jin,Wang, Peng-Yu,Xiong, De-Cai,Xue, Wan-Ying,Ye, Xin-Shan
, (2022/02/21)
The photoinitiated intramolecular hydroetherification of alkenols has been used to form C?O bonds, but the intermolecular hydroetherification of alkenes with alcohols remains an unsolved challenge. We herein report the visible-light-promoted 2-deoxyglycosylation of alcohols with glycals. The glycosylation reaction was completed within 2 min in a high quantum yield (?=28.6). This method was suitable for a wide array of substrates and displayed good reaction yields and excellent stereoselectivity. The value of this protocol was further demonstrated by the iterative synthesis of 2-deoxyglycans with α-2-deoxyglycosidic linkages up to a 20-mer in length and digoxin with β-2-deoxyglycosidic linkages. Mechanistic studies indicated that this reaction involved a glycosyl radical cation intermediate and a photoinitiated chain process.
TARGETED BIFUNCTIONAL DEGRADERS
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, (2021/04/17)
The present invention provides, in one aspect, bifunctional compounds that can be used to promote or enhance degradation of certain circulating proteins. In another aspect, the present invention provides bifunctional compounds that can be used to promote or enhance degradation of certain autoantibodies. In certain embodiments, treatment or management of a disease and/or disorder requires degradation, removal, or reduction in concentration of the circulating protein or the autoantibody in the subject. Thus, in certain embodiments, administration of a compound of the invention to the subject removes or reduces the circulation concentration of the circulating protein or the autoantibody, thus treating, ameliorating, or preventing the disease and/or disorder. In certain embodiments, the circulating protein is TNF.
ENGINEERED ANTIBODIES AS MOLECULAR DEGRADERS THROUGH CELLULAR RECEPTORS
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, (2021/04/17)
The present disclosure provides, in one aspect, bifunctional compounds that can be used to promote or enhance degradation of certain circulating proteins. In certain embodiments, the circulating protein mediates a disease and/or disorder in a subject, and treatment or management of the disease and/or disorder requires degradation, removal, or reduction in concentration of the circulating protein in the subject. Thus, in certain embodiments, administration of a compound of the disclosure to the subject removes or reduces the circulation concentration of the circulating protein, thus treating, ameliorating, or preventing the disease and/or disorder.
Ir(I)-Catalyzed C?H Glycosylation for Synthesis of 2-Indolyl-C-Deoxyglycosides
Yu, Changyue,Liu, Yichu,Xie, Xiong,Hu, Shulei,Zhang, Shurui,Zeng, Mingjie,Zhang, Dan,Wang, Jiang,Liu, Hong
supporting information, p. 4926 - 4931 (2021/09/09)
The construction of 2-deoxy-C-glycosides has gradually become a hotspot of carbohydrate chemistry in recent years. In this work, we present an efficient, regioselective, stereoselective and widely applicable strategy for the synthesis of 2-indolyl-C-deoxyglycosides via Ir(I)-catalyzed, pyridine-group-directed C?H functionalization. This method exhibits high tolerance for the functional groups of indoles and the protecting groups of carbohydrates. Moreover, this protocol has good stereoselectivity and mainly produces β-configuration products. Gram-scale synthesis and several practical transformations were conducted for further applications. Meantime, we also explored the mechanism of this method and proposed a catalytic cycle. (Figure presented.).
Rhodium-Catalyzed Denitrogenative Transannulation of N-Sulfonyl-1,2,3-triazoles with Glycals Giving Pyrroline-Fused N-Glycosides
Bi, Jingjing,Tan, Qiang,Wu, Hao,Liu, Qingfeng,Zhang, Guisheng
supporting information, p. 6357 - 6361 (2021/08/23)
Described here is a selective synthesis of 2,3-dihydropyrrole-fused N-glycosides through rhodium-catalyzed denitrogenative transannulation of N-sulfonyl-1,2,3-triazoles with glycals. A series of pyrroline-fused N-glycosides are afforded in moderate to exc
Azomethine ylide cycloaddition of 2-C-formyl glycals with α-amino acids for the synthesis of substituted pyrroles
Reddy, V. Veerabadhra,Reddy, B.V. Subba
, (2021/09/03)
A novel strategy has been devised for the synthesis of pyrrole based acyclo-C-nucleosides, in particular an open-chain sugar substituted pyrrole derivatives by means of the condensation of 2-C-formyl glycals with α-amino acids through an intramolecular azomethine cycloaddition under thermal conditions. The use of cyclic α-amino acids provides the corresponding bicyclic pyrrole derivatives. This is a first report on the synthesis of pyrrole based acyclo-C-nucleosides. 2009 Elsevier Ltd. All rights reserved.
C-2 auxiliaries for stereoselective glycosylation based on common additive functional groups
Boltje, Thomas J.,De Kleijne, Frank F. J.,Moons, Sam J.,White, Paul B.
, p. 1165 - 1184 (2020/02/22)
The stereoselective introduction of the glycosidic bond is one of the main challenges in chemical oligosaccharide synthesis. Stereoselective glycosylation can be achieved using neighbouring group participation of a C-2 auxiliary or using additives, for example. Both methods aim to generate a defined reactive intermediate that reacts in a stereoselective manner with alcohol nucleophiles. This inspired us to develop new C-2 auxiliaries based on commonly used additive functionalities such as ethers, phosphine oxides and tertiary amides. Good 1,2-trans-selectivity was observed for the phosphine oxide and amide-based auxiliaries expanding the toolbox with new auxiliaries for stereoselective glycosylation reactions.
Palladium-Catalyzed One-Pot Stereospecific Synthesis of 2-Deoxy Aryl C-Glycosides from Glycals and Anilines in the Presence of tert-Butyl Nitrite
Kandasamy, Jeyakumar,Singh, Adesh Kumar,Venkatesh, Rapelly
, p. 4215 - 4230 (2019/11/14)
The palladium-catalyzed one-pot synthesis of 2,3-deoxy-3-keto aryl C-glycosides is achieved from glycals and anilines in the presence of tert-butyl nitrite and aqueous HBF 4 under mild conditions. This one-pot method stereospecifically provides α-and β-Aryl glycosides (≥19:1 by NMR) in good yields at room temperature. The configuration at the C-3 position in the glycal determines the anomeric selectivity (i.e., α or β) of the desired products.
Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit
Keith, D. Jamin,Townsend, Steven D.
, p. 12939 - 12945 (2019/08/22)
Zwitterionic polysaccharides (ZPSs) activate T-cell-dependent immune responses by major histocompatibility complex class II presentation. Herein, we report the first synthesis of a Morganella morganii ZPS repeating unit as an enabling tool in the synthesis of novel ZPS materials. The repeating unit incorporates a 1,2-cis-α-glycosidic bond; the problematic 1,2-trans-galactosidic bond, Gal-β-(1 → 3)-GalNAc; and phosphoglycerol and phosphocholine residues which have not been previously observed together as functional groups on the same oligosaccharide. The successful third-generation approach leverages a first in class glycosylation of a phosphoglycerol-functionalized acceptor. To install the phosphocholine unit, a highly effective phosphocholine donor was synthesized.
BIFUNCTIONAL SMALL MOLECULES TO TARGET THE SELECTIVE DEGRADATION OF CIRCULATING PROTEINS
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, (2019/11/04)
The present invention is directed to bifunctional small molecules which contain a circulating protein binding moiety (CPBM) linked through a linker group to a cellular receptor binding moiety (CRBM) which is a membrane receptor of degrading cell such as a hepatocyte or other degrading cell. In embodiments, the (CRBM) is a moiety which binds to asialoglycoprotein receptor (an asialoglycoprotein receptor binding moiety, or ASGPRBM) of a hepatocyte. In additional embodiments, the (CRBM) is a moiety which binds to a receptor of other cells which can degrade proteins, such as a LRP1, LDLR, FcyRI, FcRN, Transferrin or Macrophage Scavenger receptor. Pharmaceutical compositions based upon these bifunctional small molecules represent an additional aspect of the present invention. These compounds and/or compositions may be used to treat disease states and conditions by removing circulating proteins through degradation in the hepatocytes or macrophages of a patient or subject in need of therapy. Methods of treating disease states and/or conditions in which circulating proteins are associated with the disease state and/or condition are also described herein.
