116501-53-2Relevant articles and documents
Electrochemical Synthesis of Glycosyl Fluorides Using Sulfur(VI) Hexafluoride as the Fluorinating Agent
Kim, Sungjin,Nagorny, Pavel
, p. 2294 - 2298 (2022/04/07)
This manuscript describes the electrochemical synthesis of 17 different glycosyl fluorides in 73-98% yields on up to a 5 g scale that relies on the use of SF6 as an inexpensive and safe fluorinating agent. Cyclic voltammetry and related mechanistic studies carried out subsequently suggest that the active fluorinating species generated through the cathodic reduction of SF6 are transient under these reductive conditions and that the sulfur and fluoride byproducts are effectively scavenged by Zn(II) to generate benign salts.
Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers
Gong, Liang,Sun, Hong-Bao,Deng, Li-Fan,Zhang, Xia,Liu, Jie,Yang, Shengyong,Niu, Dawen
, (2019/05/22)
We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.
Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers
Gong, Liang,Sun, Hong-Bao,Deng, Li-Fan,Zhang, Xia,Liu, Jie,Yang, Shengyong,Niu, Dawen
, p. 7680 - 7686 (2019/05/22)
We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.
Visible Light Enables Aerobic Iodine Catalyzed Glycosylation
Krumb, Matthias,Lucas, Tobias,Opatz, Till
, p. 4517 - 4521 (2019/08/06)
A versatile protocol for light induced catalytic activation of thioglycosides using iodine as an inexpensive and readily available photocatalyst was developed. Oxygen serves as a green and cost-efficient terminal oxidant and irradiation is performed with a common household LED-bulb. The scope of this glycosylation protocol was investigated in the synthesis of O-glycosides with yields up to 95 %.
Dissection of the effects that govern thioglucoside and thiomannoside reactivity
Heuckendorff, Mads,Poulsen, Lulu Teressa,Hedberg, Christinne,Jensen, Henrik H.
, p. 2277 - 2288 (2018/04/05)
Neighboring group effects were investigated in gluco- and manno-configured thioglycosides under NIS/TfOH activation. Donors possessing a 2-O-benzoyl group that are capable (1,2-trans) and incapable (1,2-cis) of exerting nucleophilic push were compared wit
Synthesis of C-spiro-glycoconjugates from sugar lactones via zinc mediated Barbier reaction
Lambu, Mallikharjuna Rao,Hussain, Altaf,Sharma, Deepak K.,Yousuf, Syed Khalid,Singh, Baldev,Tripathi, Anil. K.,Mukherjee, Debaraj
, p. 11023 - 11028 (2014/03/21)
Anomeric gem-diallylation, mono-β-crotylation and mono-β- propargylation of sugar 1,5 and 1,4 lactones have been achieved under Barbier reaction conditions using Zn powder and a catalytic amount of TMSCl as an activator. Ring closing olefin metathesis of the synthesized gem-diallyl derivatives furnished C-spiro cyclopentene glycosides. Finally, the cyclopentene rings were converted into carbohydrate based tricyclic morpholine fused triazole glycoconjugates as potential SGLT2 inhibitors.
Influence of O6 in mannosylations using benzylidene protected donors: Stereoelectronic or conformational effects?
Frihed, Tobias Gylling,Walvoort, Marthe T. C.,Codee, Jeroen D. C.,Van Der Marel, Gijs A.,Bols, Mikael,Pedersen, Christian Marcus
supporting information, p. 2191 - 2205 (2013/05/08)
The stereoselective synthesis of β-mannosides and the underlying reaction mechanism have been thoroughly studied, and especially the benzylidene-protected mannosides have gained a lot of attention since the corresponding mannosyl triflates often give exce
Acceptor-influenced and donor-tuned base-promoted glycosylation
Boettcher, Stephan,Matwiejuk, Martin,Thiem, Joachim
, p. 413 - 420 (2012/05/05)
Base-promoted glycosylation is a recently established stereoselective and regioselective approach for the assembly of di- and oligosaccharides by using partially protected acceptors and glycosyl halide donors. Initial studies were performed on partially methylated acceptor and donor moieties as a model system in order to analyze the key principles of oxyanion reactivities. In this work, extended studies on base-promoted glycosylation are presented by using benzyl protective groups in view of preparative applications. Emphases are placed on the influence of the acceptor anomeric configuration and donor reactivities.
Synthesis of thioglycosides from propargyl glycosides exploiting alkynophilic gold catalyst
Vidadala, Srinivasa Rao,Thadke, Shivaji A.,Hotha, Srinivas,Kashyap, Sudhir
experimental part, p. 241 - 251 (2012/07/27)
Various thioglycosides were synthesized from stable propargyl glycosides using catalytic quantity of AuBr3 and various thiol aglycons. The current protocol enables preparation of thioglycosides from propargyl glycosides in an efficient and simp
Highly efficient synthesis of ketoheptoses
Waschke, Daniel,Thimm, Julian,Thiem, Joachim
, p. 3628 - 3631 (2011/09/15)
A reliable, facile, high overall yielding and diastereoselective synthesis of ketoheptoses was developed and applied for preparation of the two most diabetogenic ketoheptoses as well as in a modified version for the synthesis of kamusol.