Efficient and Selective Synthesis of Glycofuranosyl Azides and Nucleosides from Cyclic 1,2-Thiocarbonate Sugars

Abstract

[reaction: see text] Cyclic 1,2-thiocarbonate sugars are convenient starting materials for the selective and efficient preparation of glycofuranosyl azides and nucleosides by regio- and stereoselective thiocarbonate ring-opening.

Synthesis and applications of the sulfur containing analogues of cyclic carbonates

“…3c). 16,17 Meanwhile, Endo and co-workers studied the synthesis of polyhydroxythiourethanes through polyaddition of a bis(cyclic thiocarbonate) species with a diamine (Fig. 3d).…”

The first example of glucose-containing carbene Brønsted acid synthesis and catalysis: efficient synthesis of five substituted tetrahydropyridines

“…83% yield. IR (KBr, ν, cm -1 ): 3245, 3025, 2920(KBr, ν, cm -1 ): 3245, 3025, , 1650(KBr, ν, cm -1 ): 3245, 3025, , 1594(KBr, ν, cm -1 ): 3245, 3025, , 1517(KBr, ν, cm -1 ): 3245, 3025, , 12501 H NMR (400 MHz, DMSO-d 6 ) δ 1.39 (t, J=7.0 Hz, 3H), 2.06 (s, 3H), 2.22 (s,3H),2.75 (dd,J=14.8 and 2.0 Hz,1H),2.88 (dd,J=15.6 and 8.4 Hz,1H),2H),5.32 (brs,1H),5H),6.81 (d,J=8.8 Hz,2H) 4,144.9,144.4,143.1,135.5,135.2,129.5,129.4,128.6,128.2,127.0,126.7,126.5,126.2,125.9,125.0,112.9,97.7,59.6,58.2,55.2,33.6,20.9,20.1,14.8;HRMS (ESI) …”

“…By far, it is mainly used as surfactant, 2 carrier to extract and separate protein from complex system 3 and substrate in asymmetric organic synthesis. 4 Although possessing five hydroxyl groups in its framework, glucose is not active enough to be an organocatalyst. Therefore, it should be functionalized and introduced active sites into its framework if we want to use it as catalyst or enhance its catalysis.…”

“…β- 3,4, 4 ] + [HSO 4 ] -, I) was synthesized for the first time and used as an efficient catalyst to prepare fivesubstituted tetrahydropyridines via the three-component condensation of aromatic aldehyde, aromatic aniline and ethyl acetoacetate in ethanol at 40°C. Six bonds were cleaved while five new bonds and one new ring were formed in one-pot with water as the only one by-product in this highly atom-economic reaction.…”

Regioselective azidotrimethylsilylation of carbohydrates and applications thereof

“…reactions of glycosyl halides with metal azides or tetramethylguanidinium azide under homogeneous conditions or by using phase transfer catalysts; 11 reactions of glycosyl esters with trimethylsilyl azide in the presence of a Lewis acid catalyst; 12 reacting cyclic 1,2-sulfite sugar derivatives 13 and thiocarbonate ring opening with NaN 3 . 14 The selective azidation of the terminal hydroxyl group in monosaccharides for the synthesis of 6-deoxy-6-azido-2,3,4-tri-O-trimethylsilyl ethers involves multiple reaction steps i.e. tosylation of primary -OH group, base mediated silylation of secondary -OH groups by TMSCl followed by stereoselective nucleophilic substitution of O-tosyl group by NaN 3 .…”