132155-06-7Relevant academic research and scientific papers
Hg(OTf)2-catalyzed glycosylation using alkynoate as the leaving group
Imagawa, Hiroshi,Kinoshita, Atsushi,Fukuyama, Takashi,Yamamoto, Hirofumi,Nishizawa, Mugio
, p. 4729 - 4731 (2006)
A novel Hg(OTf)2-catalyzed glycosylation procedure has developed using alkynoic acid residues as the leaving group under mild reaction conditions and efficient catalytic turnover. The process is particularly useful for the glycosylation of hind
Visible-light-promoted 3,5-dimethoxyphenyl glycoside activation and glycosylation
Cao, Yafei,Li, Qin,Liu, Da-Ke,Liu, Jianhui,Mao, Run-Ze,Xia, Feng,Xiong, De-Cai,Ye, Xin-Shan,Zhou, Minmin,Zou, You
, p. 10899 - 10902 (2021/10/25)
A new glycosylation method promoted by visible light with 3,5-dimethoxyphenyl glycoside as the donor was developed. This protocol delivers bothO-glycosides andN-glycosides in moderate to excellent yields using a wide range ofO-nucleophiles and nucleobases as the glycosyl acceptors.
How do Various Reaction Parameters Influence Anomeric Selectivity in Chemical Glycosylation with Thioglycosides and NIS/TfOH Activation?
Andersen, Sofie M.,Heuckendorff, Mads,Jensen, Henrik H.,Trinderup, Helle H.
, p. 3251 - 3259 (2021/06/25)
The reaction of glycosyl donor phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside with NIS/TfOH(cat.) was systematically studied under various reaction conditions. Neither the molecular sieve pore size nor amount of NIS activator was found to have a
A visible light promoted O-glycosylation with glycosyl trichloroacetimidates using eosin Y as an organo photoacid
Li, Hongfang,Liu, Jiao,Ni, Guanghui,Wang, Haimei,Yin, Shan
, (2020/03/06)
A photoacid catalyzed O-glycosylation of alcohols with glycosyl trichloroacetimidates in the presence of commercially available phenolic photoacids, fluorescein, 4′,5′-dibromo-fluorescein, and eosin Y under visible light irradiation by blue LEDs was devel
Silver-catalyzed stereoselective formation of glycosides using glycosyl ynenoates as donors
Dong, Xu,Chen, Li,Zheng, Zhitong,Ma, Xu,Luo, Zaigang,Zhang, Liming
, p. 8626 - 8629 (2018/08/06)
A silver-catalyzed glycosylation reaction employing readily accessible and stable glycosyl ynenoates is developed. This reaction is mostly high yielding and exhibits varying levels of stereoinversion at the anomeric position. Compared to established and versatile Yu's gold catalysis, this chemistry features the use of substantially cheaper AgNTf2.
Tris(pentafluorophenyl)borane-promoted stereoselective glycosylation with glycosyl trichloroacetimidates under mild conditions
Mishra, Kunj Bihari,Singh, Adesh Kumar,Kandasamy, Jeyakumar
, p. 4204 - 4212 (2018/04/14)
Tris(pentafluorophenyl)borane-promoted stereoselective glycosylation with trichloroacetimidate glycosyl donors is described. The reactions proceed efficiently with a wide range of acceptors, from sugar to nonsugar, under mild conditions in the presence of
DIDMH in combination with triflic acid - A new promoter system for thioglycoside glycosyl donors
Heuckendorff, Mads,Jensen, Henrik H.
, p. 86 - 91 (2017/12/01)
We have explored the possibility of using 1,3-diiodo-5,5-dimethylhydantoin (DIDMH) as an alternative to N-iodosuccinimide (NIS) for activation of glycosyl donors of the thioglycoside type in various glycosylation reactions. DIDMH was found to match NIS wh
Electron-deficient pyridinium salts/thiourea cooperative catalyzed O-glycosylation via activation of O-glycosyl trichloroacetimidate donors
Shaw, Mukta,Kumar, Yogesh,Thakur, Rima,Kumar, Amit
supporting information, p. 2385 - 2395 (2017/11/16)
The glycosylation of O-glycosyl trichloroacetimidate donors using a synergistic catalytic system of electron-deficient pyridinium salts/aryl thiourea derivatives at room temperature is demonstrated. The acidity of the adduct formed by the 1, 2-addition of
AuCl3-AgOTf promoted O-glycosylation using anomeric sulfoxides as glycosyl donors at room temperature
Palanivel, Ashokkumar,Chennaiah, Ande,Dubbu, Sateesh,Mallick, Asadulla,Vankar, Yashwant D.
, p. 43 - 49 (2016/12/09)
Activation of sulfoxide as glycosyl donors using AuCl3/AgOTf reagent system has been described. Under optimal reaction conditions, both armed and disarmed glycosyl sulfoxide donors were found to react with a range of primary, secondary, and tertiary alcohol acceptors, and sugar derived glycosyl acceptors to afford the corresponding glycosides in moderate to good yields with predictable selectivity. The reactions are quick (20–60 min), facile at room temperature and the reactions conditions tolerate acid sensitive groups.
Remote Electronic Effects by Ether Protecting Groups Fine-Tune Glycosyl Donor Reactivity
Heuckendorff, Mads,Poulsen, Lulu Teressa,Jensen, Henrik H.
, p. 4988 - 5006 (2016/07/06)
It was established that para-substituted benzyl ether protecting groups affect the reactivity of glycosyl donors of the thioglycoside type with the N-iodosuccinimide/triflic acid promoter system. Having electron donating p-methoxybenzyl ether (PMB) groups increased the reactivity of the donor in comparison to having electron withdrawing p-chloro (PClB) or p-cyanobenzyl ether (PCNB) protecting groups, which decreased the reactivity of the glycosyl donor relative to the parent benzyl ether (Bn) protected glycosyl donor. These findings were used to perform the first armed-disarmed coupling between two benzylated glucosyl donors by tuning their reactivity. In addition, the present work describes a highly efficient palladium catalyzed multiple cyanation and methoxylation of p-chlorobenzyl protected thioglycosides. The results of this paper regarding both the different electron withdrawing properties of various benzyl ethers and the efficient and multiple protecting group transformations are applicable in general organic chemistry and not restricted to carbohydrate chemistry.
