98906-49-1Relevant academic research and scientific papers
Glycosyl dithiocarbamates: β-selective couplings without auxiliary groups
Padungros, Panuwat,Alberch, Laura,Wei, Alexander
, p. 2611 - 2624 (2014/04/17)
In this article, we evaluate glycosyl dithiocarbamates (DTCs) with unprotected C2 hydroxyls as donors in β-linked oligosaccharide synthesis. We report a mild, one-pot conversion of glycals into β-glycosyl DTCs via DMDO oxidation with subsequent ring opening by DTC salts, which can be generated in situ from secondary amines and CS2. Glycosyl DTCs are readily activated with Cu(I) or Cu(II) triflate at low temperatures and are amenable to reiterative synthesis strategies, as demonstrated by the efficient construction of a tri-β-1,6-linked tetrasaccharide. Glycosyl DTC couplings are highly β-selective despite the absence of a preexisting C2 auxiliary group. We provide evidence that the directing effect is mediated by the C2 hydroxyl itself via the putative formation of a cis-fused bicyclic intermediate.
Comparative solution and solid-phase glycosylations toward a disaccharide library
Agoston, Karoly,Kroeger, Lars,Agoston, Agnes,Dekany, Gyula,Thiem, Joachim
experimental part, p. 1428 - 1433 (2009/12/05)
A comparative study on solution-phase and solid-phase oligosaccharide synthesis was performed. A 16-member library containing all regioisomers of Glc-Glc, Glc-Gal, Gal-Glc, and Gal-Gal disaccharides was synthesized both in solution and on solid phase. The
Synthesis of saponins using partially protected glycosyl donors
Du, Yuguo,Gu, Guofeng,Wei, Guohua,Hua, Yuxia,Linhardt, Robert J.
, p. 3627 - 3630 (2007/10/03)
(Matrix Presented) A new class of glycosyl donors having unprotected 2- and 2,4-hydroxyl groups were investigated under the standard glycosylation conditions. This approach was shown to be generally effective for the synthesis of alkyl and steroidal glyco
Stereospecific access to β-mannosides from glucose-derived 1,2-orthoesters as glycosyl donors
Kaji, Eisuke,Hosokawa, Yugo,Watanabe, Yusuke,Kobayashi, Mina,Yamakawa, Mayumi
, p. 459 - 470 (2007/10/03)
A new, stereospecific synthesis of β-mannosides from glucose-derived 1,2-orthoesters has been developed by a simple four step procedure, comprising β-specific glycosidation of the 1,2-orthoesters, 2′-O-deacetylation, 2′-O-triflation, and SN 2 type inversi
A practical synthesis of β-D-mannopyranosides
Fuerstner, Alois,Konetzki, Ingo
, p. 5721 - 5724 (2007/10/03)
An indirect yet highly efficient protocol for the β-D-mannosylation of sterically hindered alcohols is reported. Trichloroacetimidate 5 is used a key building block which is converted into the desired mannosides 9 via triflates 8 by an ultrasound promoted
