101802-96-4Relevant academic research and scientific papers
A facile synthesis of 6-deoxydapagliflozin
Shi, Yongheng,Xu, Huaqiang,Liu, Bingni,Kong, Weiling,Wei, Qunchao,Xu, Weiren,Tang, Lida,Zhao, Guilong
, p. 1903 - 1910 (2013)
A facile synthesis of a potent SGLT2 inhibitor, 6-deoxydapagliflozin, from methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-α-d-glucopyranoside in six steps with an overall yield of 50 % is described. The key steps were the reductive deiodination of the starting
SrCl2 as an efficient cocatalyst for acidic hydrolysis of methyl glycosides
Shi, Yong-Heng,Xie, Ya-Fei,Liu, Yu-Qiang,Wei, Qun-Chao,Xu, Wei-Ren,Tang, Li-Da,Zhao, Gui-Long
, p. 561 - 566 (2014)
SrCl2 was found to be the most efficient cocatalyst for the acidic hydrolysis of methyl glycosides after 26 kinds of most representative metal salts were screened. The SrCl2-cocatalyzed acidic hydrolysis of methyl glycosides is highl
Synthesis method of Tilgliflozin intermediate
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, (2021/04/17)
The invention belongs to the field of medicinal chemistry, and particularly relates to a synthesis method of a Tilgliflozin intermediate, which comprises the following steps: carrying out primary hydroxyl iodination and acetylation reaction on a compound A serving as a raw material to obtain iodinated acetate, reducing iodide into a methyl compound, preparing into a benzyl protection product, removing methyl protection, and reacting the swern oxidized hydroxyl in five steps to obtain a Tildagliflozin intermediate, namely a compound F. According to the method, the danger that in the prior art, due to the fact that selective silicon groups are adopted for protecting primary alcohol, benzyl is adopted for protecting three secondary alcohols, NaH is adopted, and consequently explosion is likely to happen is avoided, the reaction steps are further simplified, a high-yield final product can be obtained without column chromatography, and the total yield can reach 56%. The method provided by the invention is free of high-temperature and low-temperature reactions and dangerous reagents, the used raw materials are easy to obtain, the cost is greatly saved and is only 1/2-1/3 of that of a currently reported route, and the method has remarkable advantages.
Design, synthesis and biological evaluation of 6-deoxy O-spiroketal C-arylglucosides as novel renal sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes
Wang, Yibing,Lou, Yang,Wang, Jiang,Li, Dan,Chen, Hui,Zheng, Tiannan,Xia, Chunmei,Song, Xiaohan,Dong, Tiancheng,Li, Jingya,Li, Jia,Liu, Hong
, p. 398 - 416 (2019/07/19)
In this work, aiming at finding a novel, potent, and selective sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor with good pharmacokinetic profiles for the treatment of diabetes, we focus on modifying the sugar moiety of SGLT2 inhibitors, which dominates the binding with glucose binding site of hSGLT, via removing the C-6 hydroxy group to adjust the physicochemical properties and target-recognition manners of SGLT2 inhibitors. In addition, tofogliflozin containing a special O-spiroketal C-arylglucoside scaffold, displayed good efficacy and bioavailability both in animals and in humans. Therefore, a series of 6-deoxy O-spiroketal C-arylglucosides as novel SGLT2 inhibitors were designed, synthesized, and evaluated in this work. The structure-activity relationship (SAR) research on this novel series and a comprehensive in vitro and in vivo biological evaluation afforded compound 39 with high in vitro hSGLT2 inhibitory activity (IC50 = 4.5 nM), good pharmacokinetic profiles, and more remarkable efficacy in C57BL/6J mice and Sprague-Dawley rats than marketed drug tofogliflozin.
Rapid Synthesis of l-Idosyl Glycosyl Donors from α-Thioglucosides for the Preparation of Heparin Disaccharides
Herczeg, Mihály,Demeter, Fruzsina,Balogh, Tímea,Kelemen, Viktor,Borbás, Anikó
, p. 3312 - 3316 (2018/07/13)
A new methodology for the synthesis of the most challenging heparin building block has been developed. Orthogonally protected l-idosyl glycosyl donors were prepared by C5 epimerization of the corresponding thioglucosides using the hydroboration/oxidation method followed by a 4,6-acetal formation. The α-anomeric configuration was crucial, and the bulky C4 substituent was advantageous for the high l-ido diastereoselectivity. The 4,6-arylmethylene group proved to be a directing element in glycosylation, whereby stereoselective α-idosylation could be achieved by using idosyl donors without a C-2 participating group.
Iodine monochloride (ICl) as a highly efficient, green oxidant for the oxidation of alcohols to corresponding carbonyl compounds
Wei, Peng,Zhang, Datong,Gao, Zhigang,Cai, Wenqing,Xu, Weiren,Tang, Lida,Zhao, Guilong
, p. 1457 - 1470 (2015/05/20)
Iodine monochloride (ICl) was discovered to be a highly efficient, green oxidant, which can oxidize aldose hemiacetals, diarylmethanols, arylalkylmethanols, anddialkylmethanols to the corresponding aldose lactones, diarylmethanones, arylalkylmethanones, and dialkylmethanones, respectively, in high yields. ICl as a green, metal-free oxidant is characterized by mild reaction condition, short reaction time, good yield, and broad scope.
PHENYL C-GLUCOSIDE DERIVATIVE CONTAINING DEOXYGLUCOSE STRUCTURE, PREPARATION METHOD AND USE THEREOF
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Paragraph 0256; 0257; 0258, (2015/11/09)
The present invention provides a phenyl C-glucoside derivative containing a deoxyglucose structure as represented by formula I, preparation method thereof, a pharmaceutical composition comprising the same, and uses thereof in the preparation of medicament
SYNTHESIS OF CYTIDINE DIPHOSPHATE-D-QUINOVOSE
Liu, Li-da,Liu, Hung-wen
, p. 35 - 38 (2007/10/02)
The title molecule, cytidine-D-quinovose (CDP-6-deoxy-D-glucose) 1, was synthesized by two different methods from the key intermediate quinovose-1-phosphate 7 which was prepared from glucose.
Partially Benzylated Derivatives of 6-Deoxy-D-glucose
Koto, Shinkiti,Morishima, Naohiko,Mori, Yoko,Tanaka, Hitoshi,Hayashi, Seiichi,et al.
, p. 2301 - 2303 (2007/10/02)
Several partially benzylated derivatives of 6-deoxy-D-glucose (D-quinovose) were synthesized from appropriate di-O-benzyl-D-glucosides whose primary hydroxyl group is unprotected, via unimolar tosylation and subsequent reduction with LiAlH4.
Highly Stereoselective Grignard Reaction of an Aldopyranose: A Simple Synthesis of 6-Deoxy-D-idose from D-Xylose
Tsuda, Yoshisuke,Nunozawa, Tetsuji,Yoshimoto, Kimihiro
, p. 3223 - 3231 (2007/10/02)
Grignard reaction of 2,3,4-tri-O-benzyl-D-xylopyranose yielded a single product with very high stereoselectivity.A threo relationship of the newly created chiral center with respect to C2 was established by converting the product into the δ-lactone of D-ido configuration, then to the unsaturated lactone of threo configuration.The result made possible a stereoselective synthesis of 6-deoxy-D-idose from D-xylose in a small number of steps.Models accounting for the high stereoselectivity in the Grignard reaction of aldoses are discussed.Keywords - Grignard reaction; stereoselectivity; configuration of unsaturated lactones; 2,3,4-tri-O-benzyl-D-xylose; 1-deoxy-D-sorbose; 6-deoxy-D-iono-1,5-lactone; 6-deoxy-D-idose; stereocontrol models
