108739-68-0Relevant academic research and scientific papers
Reagent Controlled Stereoselective Synthesis of α-Glucans
Wang, Liming,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.,Codée, Jeroen D. C.
, p. 4632 - 4638 (2018)
The development of a general glycosylation method that allows for the stereoselective construction of glycosidic linkages is a tremendous challenge. Because of the differences in steric and electronic properties of the building blocks used, the outcome of
A Highly Stereoselective Synthesis of α-Glucosides from 1-Thioglucoside Derivative under High Pressure
Gama, Yasuo,Yasumoto, Masahiko
, p. 319 - 322 (1993)
High pressure-assisted glycosylation reaction of 2-benzothiazolyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside with various alcohols by using methyl iodide as an activator gave α-glucosides in good yield with high selectivity without any use of heavy
Stereodivergent Mannosylation Using 2- O-(ortho-Tosylamido)benzyl Group
Ding, Feiqing,Ishiwata, Akihiro,Ito, Yukishige
, p. 4833 - 4837 (2018)
We report a novel strategy for obtaining both anomers from a single mannosyl donor equipped with a C2-o-TsNHbenzyl ether (2-O-TAB) by switching reaction conditions. In particular, the formation of various β-mannosides was achieved with high selectivity by using a mannosyl phosphite in the presence of ZnI2.
Catalytic and Atom-Economic Glycosylation using Glycosyl Formates and Cheap Metal Salts
Hammelev, Christian H.,Pedersen, Christian M.,Yang, Liang
, (2020)
Benzylated glycosyl formates have been synthesized in one step from the corresponding hemiacetal or orthoester with formic acid as the sole reagent. The glycosyl formates are used as glycosyl donors under catalytic conditions with cheap metal catalysts ba
Novel dehydrative glycosylation by using acid anhydride and TMSClO4
Wakao, Masahiro,Nakai, Yoshihiko,Fukase, Koichi,Kusumoto, Shoichi
, p. 27 - 28 (1999)
Novel dehydrative glycosylation with 1-hydroxy sugars as glycosyl donors was achieved. Combination of trifluoroacetic anhydride or trichloroacetic anhydride as dehydrating agents with TMSClO4 as a Lewis acid afforded desired glycosides in good
New Synthetic Methods and Reagents for Complex Carbohydrates. VII. Syntheses and Glycosylation Reactions of Glycopyranosyl Dimethylphosphinothioate Series Having a Nonparticipating Group at the C-2 Position
Yamanoi, Takashi,Nakamura, Kazumi,Sada, Shuji,Goto, Masahiro,Furusawa, Yoji,et al.
, p. 2617 - 2622 (1993)
Several glycopyranosyl dimethylphosphinothioates having a nonparticipating group at the C-2 position could be easily prepared by reactions of the corresponding glycopyranose and dimethylphosphinothioyl chloride using butyllithium as a base in tetrahydrofu
Effective activation of 'armed' thioglycoside with a new combination of trityl tetrakis(pentafluorophenyl)borate [TrB(C6F5)4] and N-(ethylthio)phthalimide (PhthNSEt)
Jona, Hideki,Takeuchi, Kazuya,Saitoh, Terunobu,Mukaiyama, Teruaki
, p. 1178 - 1179 (2000)
Glycosylation of the 'armed' thioglycoside with various glycosyl acceptors is promoted by using a combination of stoichiometoric amount of N-(ethylthio)phthalimide (PhthNSEt) and catalytic amount of trityl tetrakis(pentafluorophenyl)borate [TrB(C6F5)4], and is successfully applied to one-pot 'armed-disarmed' sequential synthesis of trisaccharides.
One-pot preparation and activation of glycosyl trichloroacetimidates: Operationally simple glycosylation induced by combined use of solid-supported, reactivity-opposing reagents
Oikawa, Masato,Tanaka, Tatsushi,Fukuda, Naohiro,Kusumoto, Shoichi
, p. 4039 - 4042 (2004)
By the combined use of solid-supported reactivity-opposing reagents, that is, basic PTBD and acidic Nafion-SAC resins, sequential reactions consisting of glycosyl trichloroacetimidate formation and glycosylation can be effected in a one-pot ope
A novel promoter, heteropoly acid, mediated chemo- and stereoselective sulfoxide glycosidation reactions
Nagai, Hideyuki,Matsumura, Shuichi,Toshima, Kazunobu
, p. 10233 - 10237 (2000)
The chemo- and stereoselective glycosidations of sulfinylglycosides and alcohols using a heteropoly acid, H3PW12O40, as a new promoter have been developed. (C) 2000 Elsevier Science Ltd.
A stereoselective glycosidation using thioglycosides, activation by combination of N-bromosuccinimide and strong acid salts
Fukase, Koichi,Hasuoka, Atsushi,Kinoshita, Ikuko,Aoki, Yutaka,Kusumoto, Shoichi
, p. 4923 - 4932 (1995)
A stereoselective glycosidation with thioglycosides was effected under mild and neutral conditions by combined use of N-bromosuccinimide (NBS) and a catalytic amount of various strong acid salts. A combination of NBS with Ph2IOTf, Bu4NOTf, or Bu4NClO4 was advantageous for β-selective glucosidation with 2-O-acylated or 2-O-benzylated donors by virtue of either the neighboring group participation or the known solvent effect of nitrile, respectively. α-Selective glucosidation was effected by the use of a 2-O-benzylated donor in the presence of LiClO4 or LiNO3 as a catalyst in ether. Addition of silica gel to the reaction mixture increased both the α-selectivity and reaction rate.
