131156-47-3Relevant academic research and scientific papers
Process development of sotagliflozin, a dual inhibitor of sodium- Glucose cotransporter-1/2 for the treatment of diabetes
Zhao, Matthew M.,Zhang, Haiming,Iimura, Shinya,Bednarz, Mark S.,Song, Qiu-Ling,Lim, Ngiap-Kie,Yan, Jie,Wu, Wenxue,Dai, Kuangchu,Gu, Xiaodong,Wang, Youchu
, p. 2689 - 2701 (2020/11/03)
The development of an efficient manufacturing process for sotagliflozin (LX4211), a dual inhibitor of sodium- glucose cotransporter-1/2 (SGLT-1/2) for the treatment of diabetes, is described. Sotagliflozin features five contiguous chiral centers on the carbohydrate core flanked by a thioether group and a biaryl moiety. Three chiral centers are obtained from the starting material L-xylose, while the other two were established (or modified) via three highly stereoselective transformations: Luche reduction (dr: 97/3), dynamic kinetic resolution of anomeric hemiacetal (dr: 95/5), and Lewis acid-promoted thiolation (dr: 1000/ 1). Global deprotection of the resulting penultimate intermediate with catalytic sodium methoxide followed by recrystallization furnishes sotagliflozin. The longest linear sequence consists of 10 steps from L-xylose with an overall yield of 40%. This process has been performed on multi-hundred kilogram batches to satisfy the drug substance development demands.
Convergent Total Synthesis of Hikizimycin Enabled by Intermolecular Radical Addition to Aldehyde
Fujino, Haruka,Fukuda, Takumi,Nagatomo, Masanori,Inoue, Masayuki
supporting information, p. 13227 - 13234 (2020/09/01)
Hikizimycin (1), which exhibits powerful anthelmintic activity, has the most densely functionalized structure among nucleoside antibiotics. A central 4-amino-4-deoxyundecose of 1 possesses 10 contiguous stereocenters on a C1-C11 linear chain and is decora
Novel synthesis method of furan xylose derivatives
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Paragraph 0033-0035, (2019/07/04)
The invention discloses a novel synthesis method of furan xylose derivatives, which comprises the following steps: L-(-) xylose and acetone are used as starting materials, and only 2-5 equivalents ofacetone are needed under the catalysis of acholine chlor
Total Synthesis of 5-Hydroxygoniothalamin
Patpi, Santhosh Reddy,Jin, Guangyi,Kantevari, Srinivas
, p. 780 - 786 (2019/01/23)
The total synthesis of 5-hydroxygoniothalamin is achieved from commercially available l -xylose. The α,β-unsaturated-δ-lactone core is constructed in very good yield by utilizing one-carbon and two-carbon cis -Wittig olefinations and δ-lactonization using Yamaguchi conditions. Subsequent Grubbs cross-metathesis followed by desilylation results in 5-hydroxygoniothalamin.
CYCLIC DINUCLEOTIDES AS ANTICANCER AGENTS
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Paragraph 1450; 1451; 1452, (2019/02/13)
The present invention is directed to compounds of the formulae I, II and III as shown below wherein all substituents are defined herein, as well as pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.
Synthesis method for 3-deoxy-1,2-O-isopropylidene-D-xylofuranose
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Paragraph 0012, (2018/04/03)
The invention discloses a synthesis method for 3-deoxy-1,2-O-isopropylidene-D-xylofuranose. 5-O-benzoyl-3-deoxy-1,2-D-isopropylidene-D-xylofuranose is added with alkali to remove 5-site benzoate protection, so that 3-deoxy-1,2-O-isopropylidene-D-xylofuranose is obtained. In the whole route of the synthesis method, the materials are cheap and easy to obtain, reaction conditions are safer and milder, the main innovation point is the removal of the 3-site hydroxyl group, the common free radical initiation principle is not utilized, and highly toxic or difficult-to-obtain reactants, such as tributyltin hydrogen, are avoided. When the synthesis method utilizes D-xylose to prepare 3-deoxy-1,2-O-isopropylidene-D-xylofuranose, the total yield reaches 34 percent.
Glucopyranosyl derivative and application thereof in medicine
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Paragraph 0183; 0185; 0186; 0187, (2017/07/19)
The invention relates to a glucopyranosyl derivative as a sodium-dependent glucose transporter (SGLT) inhibitor, a pharmaceutical composition containing the derivative and an application thereof in medicine, and in particular to the glucopyranosyl derivative as shown in a formula (I) or a pharmaceutically acceptable salt or all stereisomers thereof, or use of the pharmaceutical composition containing the derivative and the derivative and the pharmaceutical composition for preparing medicines treating diabetes and diabetes related diseases.
A remarkable chiral recognition of racemic Mosher's acid salt by naturally derived chiral ionic liquids using 19F NMR spectroscopy
Jayachandra,Reddy, Sabbasani Rajasekhara
, p. 39758 - 39761 (2016/05/24)
A new class of d-xylose derived imidazolium-based chiral ionic liquids were designed and synthesized via simple tuning approaches. The developed chiral ionic liquids were tested for their chiral recognition properties with racemic Mosher's acid salt using 19F NMR spectroscopy. For the first time, we demonstrate the excellent enantioselective discrimination of the racemic salt using significantly less equivalents of carbohydrate derived chiral ionic liquids. We have determined the enantiomeric excess values of non-racemic mixtures of Mosher's acid salts using 19F NMR spectroscopy.
GLYCOSIDE DERIVATIVES AND USES THEREOF
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Page/Page column 53-55, (2012/11/06)
The present invention provides a compound of formula I; a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical compo
