- Electrochemical Synthesis of Glycosyl Fluorides Using Sulfur(VI) Hexafluoride as the Fluorinating Agent
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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.
- Kim, Sungjin,Nagorny, Pavel
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p. 2294 - 2298
(2022/04/07)
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- Preparation method of diabetes-treating medicine, namely ipragliflozin or derivative thereof
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The invention provides a preparation method of a diabetes-treating medicine, namely ipragliflozin or a derivative thereof. According to the preparation method, alpha-O-alkenyl sulfone is used as an electrophilic reagent for the Suzuki-Miyaura coupling reaction; the reaction raw material alpha-O-alkenyl sulfone is simple to prepare and stable in structure, and can overcome the defects of instability, preparation difficulty and the like when organic halide and sulfonic acid are used as electrophilic reagents for the Suzuki-Miyaura coupling reaction. Meanwhile, the reaction are mild in reaction conditions, compatible with a wide range of heterocyclic rings and various functional groups, high in yield and capable of realizing large-scale process production. Since alpha-O-alkenyl sulfone is used as the electrophilic reagent for the Suzuki-Miyaura coupling reaction, high-yield generation of aryl glucoside and open-chain alkenyl ether can be realized, medicines for treating type 2 diabetes mellitus, namely ipragliflozin and 2-deoxyipragliflozin can also be prepared, and the application scope of the preparation method is wide.
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Paragraph 0073; 0094-0099
(2020/11/01)
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- Visible Light Enables Aerobic Iodine Catalyzed Glycosylation
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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 %.
- Krumb, Matthias,Lucas, Tobias,Opatz, Till
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p. 4517 - 4521
(2019/08/06)
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- Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers
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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.
- Gong, Liang,Sun, Hong-Bao,Deng, Li-Fan,Zhang, Xia,Liu, Jie,Yang, Shengyong,Niu, Dawen
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- Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers
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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.
- Gong, Liang,Sun, Hong-Bao,Deng, Li-Fan,Zhang, Xia,Liu, Jie,Yang, Shengyong,Niu, Dawen
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p. 7680 - 7686
(2019/05/22)
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- Dissection of the effects that govern thioglucoside and thiomannoside reactivity
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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
- Heuckendorff, Mads,Poulsen, Lulu Teressa,Hedberg, Christinne,Jensen, Henrik H.
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p. 2277 - 2288
(2018/04/05)
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- Synthesis of C-spiro-glycoconjugates from sugar lactones via zinc mediated Barbier reaction
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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.
- Lambu, Mallikharjuna Rao,Hussain, Altaf,Sharma, Deepak K.,Yousuf, Syed Khalid,Singh, Baldev,Tripathi, Anil. K.,Mukherjee, Debaraj
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p. 11023 - 11028
(2014/03/21)
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- Influence of O6 in mannosylations using benzylidene protected donors: Stereoelectronic or conformational effects?
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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
- Frihed, Tobias Gylling,Walvoort, Marthe T. C.,Codee, Jeroen D. C.,Van Der Marel, Gijs A.,Bols, Mikael,Pedersen, Christian Marcus
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supporting information
p. 2191 - 2205
(2013/05/08)
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- Synthesis of thioglycosides from propargyl glycosides exploiting alkynophilic gold catalyst
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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
- Vidadala, Srinivasa Rao,Thadke, Shivaji A.,Hotha, Srinivas,Kashyap, Sudhir
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experimental part
p. 241 - 251
(2012/07/27)
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- Acceptor-influenced and donor-tuned base-promoted glycosylation
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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.
- Boettcher, Stephan,Matwiejuk, Martin,Thiem, Joachim
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p. 413 - 420
(2012/05/05)
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- Highly efficient synthesis of ketoheptoses
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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.
- Waschke, Daniel,Thimm, Julian,Thiem, Joachim
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p. 3628 - 3631
(2011/09/15)
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- 2′-Carboxybenzyl glycosides: glycosyl donors for C-glycosylation and conversion into other glycosyl donors
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Glycosylation of various glycosyl acceptors with 2′-carboxybenzyl (CB) 2,3,4,6-tetra-O-benzyl-β-d-glucopyranoside and CB 2,3,4,6-tetra-O-benzyl-α-d-mannopyranoside as glycosyl donors afforded α-C-glycosides exclusively or predominantly in good yields. CB
- Lee, Yong Joo,Baek, Ju Yuel,Lee, Bo-Young,Kang, Sung Soo,Park, Hye-Seo,Jeon, Heung Bae,Kim, Kwan Soo
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p. 1708 - 1716
(2007/10/03)
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- Contrasting reactivity of thioglucoside and selenoglucoside donors towards promoters: implications for glycosylation stereocontrol
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The stereochemical outcome of glycosylation reactions with model thioglycosides and selenoglycosides proved to be dependent on the source of promoter iodonium ion, with iodine giving different results to N-iodosuccinimide (NIS) alone or N-iodosuccinimide/
- van Well, Renate M.,Kaerkkaeinen, Tiina S.,Kartha, K.P. Ravindranathan,Field, Robert A.
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p. 1391 - 1397
(2007/10/03)
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- Single-step multisyntheses of glycosyl acceptors: Benzylation of n-1 hydroxyl groups of phenylthio glycosides of xylose, mannose, glucose, galactose, 2-azido-2-deoxy-glucose, and 2-azido-2-deoxy-galactose
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An array of synthons is required to access an oligosaccharide library; however, multistep and thus time-consuming synthesis is inevitable. To rapidly access such synthetic units, multiple benzylation reactions of monosaccharides under phase-transfer condi
- Suzuki, Kaori,Ohtsuka, Isao,Kanemitsu, Takuya,Ako, Takuro,Kanie, Osamu
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p. 219 - 236
(2007/10/03)
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- A straightforward synthesis of 1-adamantylmethyl glycosides, and their binding to cyclodextrins
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A single-step synthesis of 1-adamantylmethyl α- and β-glycosides starting from commercially available peracetylated monosaccharides is reported. The α- and β-glucopyranosides 1a and 1b bind to β-cyclodextrin with association constants in the order of 10s
- Charbonnier, Florence,Penades, Soledad
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p. 3650 - 3656
(2007/10/03)
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- Polyamine conjugates for treatment of infection
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The present invention relates to methods of preventing or treating an infection or disease caused by an infectious agent. The present invention also relates to the augmentation of the efficacy of existing anti-infective agents by the co-administration of the compounds described herein.
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- Glycosylated steroid derivatives for transport across biological membranes and process for making and using same
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Novel glycosylated steroid derivatives for facilitating the transport of compounds across biological membranes, either in admixture or as conjugates, are disclosed. A novel process for efficient synthesis of these glycosylated steroid derivatives, using activated glycosyl sulfoxide intermediates is provided. Methods for the permeabilization of membranes and the enhancement of the activity of predetermined compounds are also provided.
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- A facile transformation of benzylated methyl glycosides to thioglycosides
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Phenyl thioglycosides, useful glycosyl donors, were synthesized in reaction of benzylated methyl glycosides with trimethylsilylbromide and thiophenol in the presence of zinc under mild conditions.
- Przybysz,Szeja,Grynkiewicz,Priebe
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p. 1270 - 1273
(2007/10/03)
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- Catalytic O- and S-Glycosylation of 1-Hydroxy Sugars
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O-Protected 1-hydroxy sugars are effectively cross-coupled with a variety of alcohols and thiols to give the corresponding glycosides by using methoxyacetic acid and ytterbium(III) trifluoromethanesulfonate as catalytic promoters.
- Inanaga, Junji,Yokoyama, Yasuo,Hanamoto, Takeshi
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p. 1090 - 1091
(2007/10/02)
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- Lanthanoid(III) triflates as new glycosylation catalysts. Selective and efficient activation of 1-O-methoxyacetyl sugars
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The reactions of 1-O-methoxyacetyl sugars with alcohols or thiols were effectively promoted by a catalytic amount of lanthanoid(III) triflates such as Tb(OTf)3, Ho(OTf)3, Tm(OTf)3, and Yb(OTf)3 to give the corre
- Inanaga,Yokoyama,Hanamoto
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p. 2791 - 2794
(2007/10/02)
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- Activation and synthetic applications of thiostannanes. A new method for synthesis of thio- and selenoglycosides
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Exposure of thiostannane to acetyl or methyl glycosides in the presence of a catalytic amount of Bu2Sn(OTf)2 provides thioglycosides in good yields. Selenoglycosidation is achieved in a like manner by use of selenostannane.
- Sato, Tsuneo,Fujita, Yukihiro,Otera, Junzo,Nozaki, Hitosi
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p. 239 - 242
(2007/10/02)
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- Studies on Glycosides VII. A Highly Stereoselective Synthesis of 1-Thioglycosides
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A facile method for the synthesis of 1-thioglycosides using 1-α-O-trimethylsilyl-2,3,4,6,-tetra-O-benzyl-D-gluco- or manno-pyranoside by the promotion of BF3Et2O was reported.The reaction conditions were very mild, and 1-thioglycosides were obtained in hi
- Li, Zhan-Jiang,Liu, Ping-Li,Li, Zhong-Jun,Qiu, Dong-Xu,Cai, Meng-Shen
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p. 2169 - 2175
(2007/10/02)
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