153658-83-4

Upstream product

• 1092840-26-0 allyl 2-acetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-β-D-glucopyranoside 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 153658-80-1 Allyl 2-acetamido-2-deoxy-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside 
• 54400-75-8 allyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 149717-35-1 Dibenzyl 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl phosphite 

Downstream Products

• 1092840-27-1 C₄₃H₅₇NO₁₆Si 

Relevant academic research and scientific papers

Synthesis of benzaldehyde-functionalized LewisX trisaccharide analogs for glyco-SAM formation

LewisX (Lex) antigen based carbohydrate-carbohydrate interactions are mediated by complexation of metal ions. Although theoretical studies about the influence of participating hydroxyl groups in the Le x trisaccharide head group (Gal

Application and limitations of the methyl imidate protection strategy of N-acetylglucosamine for glycosylations at O-4: synthesis of Lewis A and Lewis X trisaccharide analogues

We describe here the synthesis of the allyl Lea trisaccharide antigen as well as that of an analogue of the Lex trisaccharide antigen, in which the galactose residue has been replaced by a glucose unit. Although successful fucosylations at O-4 of N-acetylglucosamine acceptors have been reported using perbenzylated thioethyl fucosyl donors under MeOTf activation, such conditions led in our case to the conversion of our acceptor to the corresponding alkyl imidates. Indeed, in this synthesis of the Lea analogue, we demonstrate that the temporary protection of the N-acetyl group as a methyl imidate is advantageous to fucosylate at O-4. In contrast, we report here that glucosylation at O-4 of an N-acetylglucosamine monosaccharide acceptor using the α-trichloroacetimidate of peracetylated glucopyranose as a donor proceeded in better yields under activation with excess BF3·OEt2 than that of the corresponding methyl imidate. Therefore, we conclude that activation of thioglycoside donors by MeOTf to glycosylate at O-4 of a glucosamine acceptor is best accomplished following the temporary protection of the N-acetyl group as a methyl imidate, especially when the donors are highly reactive and prone to degradation. In contrast, if donor and acceptor can withstand multiple equivalents of BF3·OEt2, glycosylations at O-4 of a glucosamine acceptor with a trichloroacetimidate donor does not benefit from the temporary protection of the N-acetyl group as a methyl imidate.

Glycosyl Phosphites as Glycosylation Reagents: Scope and Mechanism

The glycosylation reactions with glycosyl phosphites in the presence of catalytic amounts of TMSOTf at low temperature have been studied with different donors and acceptors for the synthesis of several glycosides, including O-glycosides, S-glycosides, C-glycosides, and glycopeptides.Mechanistic investigations of the reactions indicate that the glycosyl phosphite is activated by either TfOH or TMSOTf, depending on how the substrates are mixed.When the acceptor is treated with TMSOTf first, the glycosyl phosphite is activated by the resulting TfOH.The glycosyl phosphite can also be activated by TMSOTf directly.The best result is, however, to mix the acceptor and TMSOTf first, followed by addition of the glycosyl phosphite.