58341-69-8Relevant academic research and scientific papers
A General Approach to O-Sulfation by a Sulfur(VI) Fluoride Exchange Reaction
Ferraro, Samantha L.,Flynn, James P.,Hwang, Seung,Liu, Chao,Niu, Jia,Yang, Cangjie
supporting information, p. 18435 - 18441 (2020/08/25)
O-sulfation is an important chemical code widely existing in bioactive molecules, but the scalable and facile synthesis of complex bioactive molecules carrying O-sulfates remains challenging. Reported here is a general approach to O-sulfation by the sulfur(VI) fluoride exchange (SuFEx) reaction between aryl fluorosulfates and silylated hydroxy groups. Efficient sulfate diester formation was achieved through systematic optimization of the electronic properties of aryl fluorosulfates. The versatility of this O-sulfation strategy was demonstrated in the scalable syntheses of a variety of complex molecules carrying sulfate diesters at various positions, including monosaccharides, disaccharides, an amino acid, and a steroid. Selective hydrolytic and hydrogenolytic removal of the aryl masking groups from sulfate diesters yielded the corresponding O-sulfate products in excellent yields. This strategy provides a powerful tool for the synthesis of O-sulfate bioactive compounds.
HClO4-silica-catalysed regioselective opening of benzylidene acetals and its application towards regioselective HO-4 glycosylation of benzylidene acetals in one-pot
Dara, Saidulu,Saikam, Varma,Yadav, Mahipal,Singh, Parvinder Pal,Vishwakarma, Ram A.
supporting information, p. 93 - 96 (2014/05/20)
Here we report a high-yielding method for the regioselective reductive ring opening of 4,6-O-benzylidene acetals of hexapyranosides using inexpensive and robust HClO4-SiO2 as the acidic catalyst and triethylsilane as the hydride dono
Carbohydrate-based crown ethers containing 1,4-linked D-glucopyranose moieties
Miethchen,Fehring
, p. 94 - 98 (2007/10/03)
The chiral crown ethers 7, 8, 9, and 13 containing a 1,4-bridged α-D-glucopyranose moiety were synthesized from methyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside (1) and methyl 2,3-di-O-allyl-6-O-benzyl-α-D-glucopyranoside (2), respectively, by two subsequent etherification reactions followed by an intramolecular transglycosylation. To build up the hexaethylene glycol chain in 4-position of 1 and 2, bis(2-chloroethyl) ether (generating 3 and 4, respectively) and tetraethylene glycol (yielding 5 and 6, respectively) were used. The cyclizations of 5 and 6 in acetonitrile to the crowns 7 and 8 were catalysed by trimethylsilyl trifluoromethanesulfonate assisted by a 'template' effect of potassium tetrafluoroborate (yield 45-57percent). A high a-stereoselectivity was found for the intramolecular glycosylations even if a benzoylated precursor such as 12 was cyclized (catalyst: BF3 Et2O; yield 25-26percent). Compound 12 was prepared from 5 by exchange of the benzyl groups for benzoyl functions (10-12). Finally, the crown ether 8 was deallylated to generate the crown 9.
