61025-08-9Relevant academic research and scientific papers
Stereoselective syntheses of 1,2-trans p-MePh and 2-pyridyl 1- thioglycosides catalyzed by zirconium(IV) chloride
Ding, Yili
, p. 3541 - 3546 (1999)
1-Thioglycosides including per-O-acetyl p-MePh and 2-pyridyl 1- thioglycosides were chemically synthesized with high complete stereoselectivity by using ZrCl4 as catalyst.
Synthesis and Antiproliferative Activities of OSW-1 Analogues Bearing 2”-O-p-Acylaminobenzoyl Residues?
Sun, Lijun,Zhu, Di,Beverborg, Laura Olde Groote,Wang, Ruina,Dang, Yongjun,Ma, Mingming,Li, Wei,Yu, Biao
, p. 1091 - 1097 (2020)
OSW-1 is a well-known natural saponin with potent antitumor activities. We have designed and prepared a small library of 22 OSW-1 analogues with a variety of p-acylamino-benzoyl groups installed at C2” of the xylose residue, wherein a regioselective (1→3)
Concise Synthesis of 1-Thioalkyl Glycoside Donors by Reaction of Per-O-acetylated Sugars with Sodium Alkanethiolates under Solvent-Free Conditions
Dong, Hai,Feng, Guang-Jing,Guo, Yang-Fan,Liu, Chun-Yang,Luo, Tao
, (2022/02/07)
A relatively green method for synthesizing 1-thioalkyl glycosides has been developed, where sodium alkanethiolates were used to react with per-O-acetylated sugars instead of odorous alkyl mercaptans in the presence of BF3·Et2O without the use of solvents under mild conditions. Furthermore, we found that 1,2-trans-β-thioglycosides can be converted into corresponding 1,2-cis-α-thioglycosides in the presence of trifluoromethanesulfonic acid in nonpolar solvents under mild conditions. This provides a simple and efficient new approach for synthesizing challenging 1,2-cis-α-thioglycosides.
Tailormade Polysaccharides with Defined Branching Patterns: Enzymatic Polymerization of Arabinoxylan Oligosaccharides
Senf, Deborah,Ruprecht, Colin,Kishani, Saina,Matic, Aleksandar,Toriz, Guillermo,Gatenholm, Paul,W?gberg, Lars,Pfrengle, Fabian
, p. 11987 - 11992 (2018/09/10)
The heterogeneous nature of non-cellulosic polysaccharides, such as arabinoxylan, makes it difficult to correlate molecular structure with macroscopic properties. To study the impact of specific structural features of the polysaccharides on crystallinity
InBr 3 -Catalyzed Synthesis of Aryl 1,2- trans -Thio(seleno)glycosides
Ma, Teng,Li, Changwei,Liang, Haijing,Wang, Zhaoyan,Yu, Lan,Xue, Weihua
supporting information, p. 2311 - 2314 (2017/10/06)
InBr 3 is demonstrated to be an efficient catalyst for reactions of fully acetated aldoses with aryl mercaptans or selenophenol at room temperature, rapidly furnishing the corresponding thioglycosides or selenoglycosides with exclusively 1,2- t
A Kinsenoside and GoodyerosideA analogs of the preparation and use thereof
-
Paragraph 0035; 0036; 0037; 0038; 0039, (2017/06/14)
The invention discloses a preparation method and application of compounds as shown in formula I and II, and in particular relates to preparation of Kinsenoside or GoodyerosideA analogue and medical application of the Kinsenoside or GoodyerosideA analogue
A facile and efficient method for the one-pot synthesis of per-O-acetylated thioglycosides from unprotected sugars
Yan, Shiqiang,Ding, Ning,Zhang, Wei,Wang, Peng,Li, Yingxia,Li, Ming
, p. 571 - 583 (2012/10/30)
An efficient, convenient protocol for the preparation of per-O-acetylated p-tolylthio glycosides is described. Treatment of various unprotected sugars, including 2-deoxy-2-amino sugars, sialic acid, lactose, and maltose, with acetic anhydride using SnCl4 as a catalyst, and subsequently with p-tolylthiol, furnished the corresponding thioglycosides in 71%-90% yield under solvent-free conditions.
Chemical synthesis of a heparan sulfate glycopeptide: Syndecan-1
Yang, Bo,Yoshida, Keisuke,Yin, Zhaojun,Dai, Hang,Kavunja, Herbert,El-Dakdouki, Mohammad H.,Sungsuwan, Suttipun,Dulaney, Steven B.,Huang, Xuefei
, p. 10185 - 10189,5 (2012/12/12)
Finishing first: The highly complex structure of the title compound (see picture) was assembled. The protective groups utilized, as well as the sequences for formation of the glycosyl linkages and protecting group removal are critical to the success of the synthesis. This first preparation of a heparan sulfate glycopeptide lays the foundation for accessing other members of this class of molecules. Copyright
Lanthanum trifluoromethane-sulfonate-catalyzed facile synthesis of per-O-acetylated sugars and their one-pot conversion to S-aryl and O-alkyl/aryl glycosides
Dasgupta, Somnath,Rajput, Vishal Kumar,Roy, Bimalendu,Mukhopadhyay, Balaram
, p. 91 - 106 (2008/02/09)
Lanthanum trifluoromethanesulfonate-catalyzed solvent-free per-O-acetylation with stoichiometric acetic anhydride proceeds in high yield (95%-99%) to afford exclusively pyranose products as anomeric mixtures. Subsequent anomeric substitution employing borontrifluoride etherate and thiols or alcohols furnished the corresponding 1,2-trans-linked thioglycosides and O-glycosides, respectively, in good to excellent overall yield (75%-85%). Alternatively, reaction of free sugars in neat alcohol employing the same catalyst at elevated temperature gives the corresponding 1,2-cis-linked O-glycosides (along with 1,2-trans-linked glycosides as minor product) in good yield (73%-80%). Anomeric mixtures of compounds thus produced were characterized as their per-O-acetylated derivatives.
