6160-67-4Relevant articles and documents
Highly regioselective and stereoselective synthesis of C-Aryl glycosidesvianickel-catalyzedortho-C-H glycosylation of 8-aminoquinoline benzamides
Shi, Wei-Yu,Ding, Ya-Nan,Zheng, Nian,Gou, Xue-Ya,Zhang, Zhe,Chen, Xi,Luan, Yu-Yong,Niu, Zhi-Jie,Liang, Yong-Min
supporting information, p. 8945 - 8948 (2021/09/10)
C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzedortho-CAr-H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows great functional group compatibility with various glycosides, showing its synthetic potential. Mechanistic studies indicate that C-H activation could be the rate-determining step.
Synthesis of triazolylmethyl-linked nucleoside analogs via combination of azidofuranoses with propargylated nucleobases and study on their cytotoxicity
Halay, Erkan,Ay, Emriye,?alva, Emine,Ay, Kadir,Karay?ld?r?m, Tamer
, p. 158 - 166 (2018/04/02)
[Figure not available: see fulltext.] Copper(I)-catalyzed azide–alkyne 1,3-dipolar cycloaddition reactions (CuAAC) between azidofuranoses and propargyl-nucleobases were carried out in the presence of CuSO4·5H2O and sodium ascorbate as catalytic system to provide the corresponding 1,4-disubstituted-1,2,3-triazole-bridged nucleoside analogs in good yields. Twelve new sugar-based triazolylmethyl-linked nucleoside analogs were synthesized and screened for their cytotoxic activity against MDA-MB-231, Hep3B, PC-3, SH-SY5Y, and HCT-116 cancer cell lines and control cell line (L929). Most of the compounds were moderately effective against all the cancer cell lines assayed. Particularly, among the tested compounds, 1,2,3-triazole-linked 5-fluorouracil–mannofuranose hybrid was found to be the most potent cytotoxic agent against HCT-116, Hep3B, SH-SY5Y cells with IC50 values of 35.6, 71.1, and 75.6 μM, respectively. None of the triazolylmethyl-linked nucleoside analogs exhibited cytotoxic effect against the control cells L929.
Solvent-free synthesis of glycosyl chlorides based on the triphenyl phosphine/hexachloroacetone system
Traboni, Serena,Liccardo, Federica,Bedini, Emiliano,Giordano, Maddalena,Iadonisi, Alfonso
, p. 1762 - 1764 (2017/04/13)
Glycosyl chlorides, useful as glycosyl donors in glycoside synthesis and precursors in organic synthesis, can be easily prepared under solvent-free conditions by exposing a sugar hemiacetal to an equimolar mixture of PPh3 and hexachloroacetone
A mild and general method for preparation of α-glycosyl chlorides
Chang, Chih-Wei,Chang, Shih-Sheng,Chao, Chin-Sheng,Mong, Kwok-Kong T.
supporting information; experimental part, p. 4536 - 4540 (2009/12/03)
A mild and efficient chlorination method for production of glycosyl chlorides is first described which employs inexpensive trichlorotriazine (TCT) and DMF as a chlorination reagent and is compatible with typical acid-labile hydroxyl protecting functions. The scope and limitations, reaction mechanism and its application in the sequential glycosylations are discussed.
Norrisolide: Total synthesis and related studies
Brady, Thomas P.,Kim, Sun Hee,Wen, Ke,Kim, Charles,Theodorakis, Emmanuel A.
, p. 7175 - 7190 (2007/10/03)
A stereoselective synthesis of (+)-norrisolide is presented. This natural product belongs to a family of marine spongiane diterpenes the structure of which is characterized by a fused γ-lactone-γ-lactol ring system attached to a bicyclic hydrophobic core.
REACTIONS OF HYDROXYL GROUPS WITH TOSYLCHLORIDE-DIMETHYLAMINOPYRIDINE SYSTEM. DIRECT SYNTHESIS OF CHLORIDES FROM HYDROXYCOMPOUNDS.
Hwang, C. K.,Li, W. S.,Nicolau, K. C.
, p. 2295 - 2296 (2007/10/02)
The reactions of various hydroxyl groups with tosylchloride-dimethylaminopyridine system were investigated and direct synthesis of allyl, alkyl and glycosyl chlorides are described.
The Reaction of N-Dichloromethylene-N,N-dialkylammonium Chlorides with Free Sugars: an Efficient Synthesis of Glycosyl Chlorides
Copeland, Christopher,McAdam, David P.,Stick, Robert V.
, p. 1239 - 1247 (2007/10/02)
The treatment of aldose derivatives that are protected at all but the anomeric hydroxy groups with N-dichloromethylene-N,N-dialkylammonium chlorides (alkyl = Me, Et) provides an improved method of preparing the corresponding glycosyl chlorides.Analogous derivatives containing an unprotected C1-C2 diol give 2-O-(N,N-dialkylcarbamoyl)glycosyl chlorides.