916596-71-9

Upstream product

• 545-06-2 trichloroacetonitrile 
• 3150-20-7 4-methoxyphenyl β-D-galactopyranoside 
• 612844-17-4 phenyl 2,3-di-O-benzoyl-4,6-O-di-tert-butylsilanediyl-1-thio-β-D-galactopyranoside 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 85272-31-7 di-tert-butylsilyl bis(trifluoromethanesulfonate) 
• 916596-69-5 C₃₅H₄₂O₉Si 

Downstream Products

• 916596-75-3 C₇₈H₁₁₅NO₁₃Si 
• 916596-77-5 C₇₁H₁₀₉NO₁₁Si 
• 1449333-12-3 allyl 2,3-di-O-benzoyl-4,6-O-di-tert-butylsilyl-α-D-galactosyl-(1→3)-2-O-benzoyl-4,6-O-benzylidene-β-D-galactoside 
• 1449333-13-4 allyl 2,3-di-O-benzoyl-α-D-galactosyl-(1→3)-2-O-benzoyl-4,6-O-benzylidene-β-D-galactoside 
• 1449333-14-5 allyl 2,3-di-O-benzoyl-α-D-galactosyl-(1→3)-2-O-benzoyl-β-D-galactoside 
• 1449333-15-6 3-(acetylthio)propyl 2,3-di-O-benzoyl-α-D-galactosyl-(1→6)-2-O-benzoyl-β-D-galactoside 

Relevant academic research and scientific papers

Synthesis of a 1,2-: Cis -indoxyl galactoside as a chromogenic glycosidase substrate

A synthetically challenging 1,2-cis-indoxyl galactoside, X-α-galactoside, was first prepared in this study using a cyclic ketone indoxyl acceptor and a glycosyl trichloroacetimidate donor to produce an enol glycoside and a 4,6-O-di-tert-butylsilylene-protected galactosyl donor to complete the synthesis. The target compound shows enzyme activity in the presence of α-galactosidase.

Extended applications of di-tert-butylsilylene-directed α-predominant galactosylation compatible with C2-participating groups toward the assembly of various glycosides

The high versatility of di-tert-butylsilylene(DTBS)-directed α-predominant galactosylation have been extended to the construction of difficult glycan sequences. First, to investigate the compatibility of the α-predominant reaction with various glycosylation systems a variety of 4,6-O-DTBS-tethered galactosaminyl or galactosyl donors were synthesized efficiently, which have C2-participating groups with a wide variety of leaving groups such as alkylsulfenyl, halide, trichloroacetimidate groups. The results of the detailed examination of the glycosylation reaction using the glycosyl donors showed the wide scope of the 4,6-DTBS-directed α-galactosylation. In the next step, the stereoselective construction of α GalN-Ser/Thr sequences was examined by employing the DTBS-directed glycosylation. As a result, various types of serine and threonine derivatives were glycosylated α-selectively, producing α-GalN-Ser/Thr sequences in high yields. Moreover, the DTBS-directed galactosylation was successfully applied for the synthesis of α-tetrasaccharyl-Ser segment of glycophorin A.

A novel synthetic route to α-galactosyl ceramides and iGb3 using DTBS-directed α-selective galactosylation

A novel synthetic route to α-galactosyl ceramides and isoglobotrihexosylceramide (iGb3), which can activate NKT cells, was developed by exploiting a di-tert-butylsilylene-directed α-selective galactosylation procedure. Georg Thieme Verlag Stuttgart.