2160551-35-7

Upstream product

• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 176299-96-0 4-methoxyphenyl 4,6-O-benzylidene-β-D-galactopyranoside 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 319922-17-3 p-methoxyphenyl 3-O-allyl-α-D-mannopyranoside 
• 28541-75-5 p-methoxyphenyl α-D-mannopyranoside 
• 17042-40-9 4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-1-α-D-mannopyranoside 
• 319922-20-8 (2R,4aR,6R,7S,8R,8aR)-8-Allyloxy-6-(4-methoxy-phenoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 150-76-5 4-methoxy-phenol 

Relevant academic research and scientific papers

1,3-syn-Diaxial Repulsion of Typical Protecting Groups Used in Carbohydrate Chemistry in 3-O-Substituted Derivatives of Isopropyl d -Idopyranosides

The strength of 1,3-syn-diaxial repulsion was evaluated for main types of protecting groups (alkyl, silyl, and acyl) usually used in carbohydrate chemistry. As molecular probes for this study, derivatives of isopropyl 2-O-benzyl-4,6-O-benzylidene-α-d-idop

Synthesis of a new glycosphingolipid from the marine ascidian Microcosmus sulcatus using a one-pot glycosylation strategy

A novel neutral glycosphingolipid found in Microcosmus sulcatus containing a β-d-Galp(1→4)[α-d-Fucp-(1→3)]β-d-Glcp-(1→)Cer motif was synthesized. Trisaccharide derivatives were synthesized using trimethylsilyltrifluoromethanesulfanate (TMSOTf) and N-iodosuccimide (NIS)/trifluoromethane sulfonic acid (TfOH) as the promoters. Synthesis was achieved with an efficient one-pot glycosylation strategy. This is the first report of a one-pot glycosylation strategy using the procedure of Boons et al. for the synthesis of a natural product. Coupling of trisaccharide derivative 19 and ceramide derivative 20 by TMSOTf afforded the glycosphingolipid derivative 21. The fully protected glycoside was deprotected to give the target glycosphingolipid 2.

Can preferential β-mannopyranoside formation with 4,6-O-benzylidene protected mannopyranosyl sulfoxides be reached with trichloroacetimidates?

Studies with 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl sulfoxide (3d) and the corresponding trichloroacetimidate (4) as glycosyl donors and various acceptors (A-F) led under similar reaction conditions to similar glycosylation results, i.e. mainly or exclusively the β-anomers of glycosides 5dA-5dF could be obtained. Thus, the versatile building block 5dA for N-glycan synthesis is readily available. For the activation of the sulfoxide leaving group, one equivalent of Tf2O and two equivalents of DTBMP are required, whereas for trichloroacetimidate activation catalytic amounts of TMSOTf are sufficient; hence, the trichloroacetimidate based procedure is very convenient. Various parameters were modified in the reaction of 4 with A (catalyst concentration, configuration of 4, size of the 2-O-protective group, solvent), thus, a proposal for the reaction course was derived. (C) 2000 Elsevier Science Ltd.