20786-72-5Relevant academic research and scientific papers
Stannous chloride as a low toxicity and extremely cheap catalyst for regio-/site-selective acylation with unusually broad substrate scope
Dong, Hai,Feng, Guang-Jing,Luo, Tao,Lv, Jian,Yu, Jian-Cheng
supporting information, p. 6936 - 6942 (2020/11/09)
This work reports stannous chloride (SnCl2)-catalyzed regio-/site-selective acylation with unusually broad substrate scope. In addition to 1,2- and 1,3-diols and glycosides containing cis-vicinal diol, the substrate scope also includes glycosides without cis-vicinal diol. For such a substrate scope, usually, only methods using stoichiometric amounts of organotin reagents can lead to the same protection pattern with high selectivities and highly isolated yields (84-97% in most cases). Therefore, SnCl2, as a low toxicity and extremely cheap reagent, should be the best catalyst for regio-/site-selective acylation compared with any previously reported reagents. This journal is
DBN-Catalyzed Regioselective Acylation of Carbohydrates and Diols in Ethyl Acetate
Ren, Bo,Zhang, Mengyao,Xu, Shijie,Gan, Lu,Zhang, Li,Tang, Lin
supporting information, p. 4757 - 4762 (2019/07/31)
The 1,5-diazabicyclo[4.3.0]non-5-ene (DBN)-catalyzed regioselective acylation of carbohydrates and diols in ethyl acetate has been developed. The hydroxyl groups can be selectively acylated by the corresponding anhydride in EtOAc in the presence of a catalytic amount (as low as 0.1 equiv.) of DBN at room temperature to 40 °C. This method avoids metal catalysts and toxic solvents, which makes it comparatively green and mild, and it uses less organic base compared with other selective acylation methods. Mechanism studies indicated that DBN could catalyze the selective acylation of hydroxyl moieties through a dual H-bonding interaction.
A green and convenient method for regioselective mono and multiple benzoylation of diols and polyols
Zhang, Xiaoling,Ren, Bo,Ge, Jiantao,Pei, Zhichao,Dong, Hai
, p. 1005 - 1010 (2016/02/03)
An efficient method for regioselective benzoylation of diols and polyols was developed. The benzoylation is catalyzed by only 0.2 equiv of benzoate anion in acetonitrile with the addition of a stoichiometric amount of benzoic anhydride under very mild condition, leading to high yields. Compared with all other methods, this method shows particular advantage in regioselective multiple benzoylation of polyols, and in avoiding the use of any metal-based catalysts and any amine bases, which is more environment-friendly.
Vinyl bis-sulfone methodology in thiosugars: selective access to chiral thiovinyl sulfones and PSE oxathianes
Chéry, Florence,Pillard, Christelle,Tatibou?t, Arnaud,De Lucchi, Ottorino,Rollin, Patrick
, p. 5141 - 5151 (2007/10/03)
Based on the vinyl bis-sulfone methodology previously developed to synthesize PSE acetals, an original approach to homochiral carbohydrate-derived PSE 1,3-oxathianes is described. The ready formation of intermediate phenylsulfonylvinyl sulfides, which hav
Synthesis of rhamnogalacturonan I oligosaccharides: Synthesis of a tetrasaccharide intermediate
Rich, Jamie R.,McGavin, Robert S.,Gardner, Rebecca,Reimer, Kerry B.
, p. 17 - 20 (2007/10/03)
A hydroxyl protected tetrasaccharide intermediate, corresponding to a segment of the rhamnogalacturonan I polysaccharide, has been synthesized using the glycosyl imidate technique. This tetrasaccharide is designed to allow for further elongation and branching.
Bausteine von Oligosacchariden, XXII. Synthese der Trisaccharid-Sequenz α-D-GlcNAc-(1-4)-β-D-Gal-(1-4)-D-GlcNAc aus blutgruppenaktiven Substanzen
Paulsen, Hans,Schnell, Dagmar
, p. 333 - 345 (2007/10/02)
A directly stereoselective α-glycoside synthesis to oligosaccharides succeeds in the presence of AgClO4/Ag2CO3 in methylene chloride with the α-bromide 1 of 2-azido-2-desoxy-D-glucose.By reaction with 1 the disaccharides 3, 7a, 7b, 18 and the trisaccharid
