612844-08-3

Upstream product

• 868230-98-2 phenyl 2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside 
• 868230-99-3 phenyl 2-deoxy-4,6-O-di-tert-butylsilylene-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside 
• 17341-93-4 2,2,2-Trichloroethyl chloroformate 
• 85272-31-7 di-tert-butylsilyl bis(trifluoromethanesulfonate) 

Downstream Products

• 612844-16-3 phenyl 2-acetamido-3-O-acetyl-2-deoxy-4,6-O-di-tert-butylsilylene-β-D-galactopyranoside 
• 1603850-70-9 5-benzyloxycarbonylamino-1-pentyl[2-deoxy-4,6-O-di-tert-butylsilylene-2-(2,2,2-trichloroethoxycarbamoyl)-3-O-(2,2,2-trichloroethoxycarbonyl)-α-D-galactopyranosyl]-(1→3)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1→2)]-(4,6-di-O-acetyl-β-D-galactopyranosyl)-(1→4)-3,6-di-O-acetyl-2-deoxy-2-phthalimide-β-D-glucopyranoside 

Relevant academic research and scientific papers

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.

METHOD OF ALPHA-SELECTIVE GLYCOSYLATION

An α-selective glycosylation process of a glycosylation reaction between a sugar structure of hexose or an aldose having a chain with six or more carbon atoms in the molecule, which is a monosaccharide or a reducing end of an oligosaccharide with two or m

Di-tert-butylsilylene (DTBS) group-directed α-selective galactosylation unaffected by C-2 participating functionalities

We have discovered an unusual α-galactosylation using phenylthioglycoside of 4,6-O-di-tert-butylsilylene (DTBS)-protected galactose derivatives as a glycosyl donor, which was not hampered by the neighboring participation of C-2 acyl functionality such as NTroc and OBz. The power of the DTBS effect has been exemplified by the coupling reaction with various glycosyl acceptors.