158325-38-3

Upstream product

• 108-98-5 thiophenol 
• 118711-49-2 1,2,4,6-tetra-O-acetyl-3-O-benzyl-L-idopyranoside 
• 108-24-7 acetic anhydride 

Downstream Products

• 175978-39-9 phenyl 3-O-benzyl-1-thio-α-L-idopyranoside 
• 1021490-96-9 C₃₃H₃₀O₆S 
• 616876-73-4 methyl (phenyl 2-O-benzoyl-3-O-benzyl-1-thio-α-L-idopyranoside)uronate 
• 1610791-08-6 C₄₂H₃₆O₉S 
• 1610791-13-3 methyl O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-(4-(((9H-fluoren-9-yl)methoxy)carbonyloxy)-α-L-idopyranosyluronate)-(1→4)-2-azido-6-O-benzoyl-3-benzyl-2-deoxy-α-D-glucopyranoside) 
• 850637-33-1 phenyl 2-O-benzoyl-3-O-benzyl-1-thio-α-L-idopyranosyluronic acid 
• 735326-98-4 phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-L-idopyranoside 
• 862607-80-5 1,6-Bis-O-(2,4,6-tri-O-acetyl-3-O-benzyl-α-L-idopyranosyl)-2,5-anhydro-3,4-di-O-benzoyl-D-mannitol 
• 175978-41-3 phenyl 2-O-benzoyl-3-O-benzyl-4,6-dihydroxylthio-α-L-idopyranoside 
• 735327-07-8 3-O-(2-O-acetyl-3,4-di-O-benzoyl-6-O-t-butyldimethylsilyl-α-L-idopyranosyl)-2,5-anhydro-1,4,6-tri-O-benzoyl-D-mannitol 
• 767287-62-7 2,5-anhydro-1,4,6-tri-O-benzoyl-3-O-(2-O-acetyl-3,4-di-O-benzoyl-α-L-idopyranosyluronic acid)-D-mannitol 
• 735327-10-3 3-O-(2-O-acetyl-3,4-di-O-benzoyl-α-L-idopyranosyl)-2,5-anhydro-1,4,6-tri-O-benzoyl-D-mannitol 
• 735327-02-3 3-O-(2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-α-L-idopyranosyl)-2,5-anhydro-1,6-di-O-benzoyl-D-mannitol 
• 781657-66-7 C₃₄H₄₆O₁₃Si 

Relevant academic research and scientific papers

Total synthesis of anticoagulant pentasaccharide fondaparinux

The anticoagulant pentasaccharide fondaparinux was synthesized using an improved and optimized synthetic strategy including a convergent [3+2] coupling approach, orthogonal protecting groups and various glycosyl donors. The new methods of glycosylation were also used for controlling the stereochemical configuration and improving the yield of the glycosylation. In addition, HPLC and NMR methods to monitor the process of total synthesis of fondaparinux were employed. This work provides a comprehensive elaboration for the synthesis and analysis of fondaparinux based on related literature, as well as abundant information for the synthesis of heparin-like oligosaccharides. A matter of protection! The anticoagulant pentasaccharide fondaparinux was synthesized using an improved and optimized synthetic strategy. The process of total synthesis was monitored by HPLC and NMR. This work will contribute to continued improvement of the multistep production of fondaparinux and provide abundant information for the synthesis of heparin-like oligosaccharides.

An efficient synthesis of l-idose and l-iduronic acid thioglycosides and their use for the synthesis of heparin oligosaccharides

Efficient preparations of thioglycoside derivatives of l-idose and l-iduronic acid are described. The method avoids the tedious chromatographic separations of furanose and pyranose anomeric mixtures, and affords the thioglycosides in a stereoselective man

Synthesis of 2,5-anhydro-(β-D-glucopyranosyluronate)- and (α-L-idopyranosyluronate)-D-mannitol hexa-O-sulfonate hepta sodium salt

Glycosidation of 2,5-anhydro-1,6-di-O-benzoyl-D-mannitol with methyl(2,3,4-tri-O-acetyl-α-D-glucopyranosyl-1-O-trichloroacetimidate) uronate in the presence of trimethylsilyl triflate afforded the corresponding 3-O-β-glycoside, which after deprotection wa

L-Iduronic acid derivatives as glycosyl donors

O-[Methyl (2-O-acetyl-3-O-benzyl-4-O-levulinyl-α, and β-L-idopyranosid)uronate]trichloroacetimidate and the corresponding n-pentenyl glycosides are efficient L-iduronic acid glycosyl donors. Both have been used for the high-yielding synthesis of basic disaccharide blocks which are useful for the subsequent synthesis of complex oligosaccharides related to heparin/heparan sulfate, and dermatan sulfate. In contrast, the corresponding thioethyl glycosides, thiophenyl glycosides, and fluoride, did not yield the expected disaccharides.