133411-35-5

Upstream product

• 3616-19-1 1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 
• 931-59-9 benzenesulfenyl chloride 
• 146788-09-2 ethyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside 
• 146815-51-2 C₃₂H₅₄O₁₃S 
• 178873-67-1 2,2-Dimethyl-propionic acid (3aS,4R,6S,7R,7aR)-6-[(2R,3S,4R,5R,6S)-2-(2,2-dimethyl-propionyloxymethyl)-6-ethylsulfanyl-4,5-dihydroxy-tetrahydro-pyran-3-yloxy]-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester 
• 146788-10-5 ethyl (3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-1-thio-β-D-glucopyranoside 
• 131070-86-5 ethyl 4-O-β-galactopyranosyl-1-thio-β-D-glucopyranoside 
• 20298-34-4 methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosyl)onate 
• 3282-30-2 pivaloyl chloride 
• 73960-72-2 methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 
• 120104-58-7 (2S,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-chloro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 146815-46-5 (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-fluoro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 133411-34-4 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-6-(2,2-dimethyl-propionyloxymethyl)-5-[(2S,3R,4S,5R,6R)-6-(2,2-dimethyl-propionyloxymethyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy]-2-ethylsulfanyl-4-hydroxy-tetrahydro-pyran-3-yl ester 

Downstream Products

• 133411-36-6 ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosylonate)-(2->3)-2,4-di-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3-O-acetyl-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

An efficient short-step total synthesis of ganglioside GM3: Effective usage of the neighbouring group participation strategy

We have developed an efficient methodology for highly stereoselective sialylation using 3-position substituted sialic acids and have prepared 2a having a 3β-phenylthio group as a sialic donor. Glycosylation of suitably protected lactoside 3 with 2a gave only the α-sialyl trisaccharide 16 in good yield. Condensation of the azidosphingosine 4 with the acetate 17 using promotors, DMTST or NIS-TfOH, afforded the glycolipid 18, which was directly transformed to 20 by reduction with Bu3P and subsequent acylation with octadecanoic acid in the presence of WSC. Removal of the protecting groups generated ganglioside CM3 (1).

Simple construction of Neu5Ac(α2-8)Neu5Ac and total synthesis of ganglioside GD3

Glycosylation of an 8-unprotected sialyl fluoride 16 with 2β-chloro-3β-phenylthio-Neu5Ac 2 gave the desired α-disialate 23. Subsequent glycosylation of a thiolactoside 19 with the disialyl fluoride 23 gave the tetrasaccharide 28. Synthesis of GD3 1 was realized by condensation of the tetrasaccharide 28 with azidosphingosine 31, following our previously reported GM3 synthesis procedure.

Total synthesis of GD3, a ganglioside

On the basis of new methodology involving α-stereo-controlled sialylation using our 2-halo-3β-phenylthio-Neu5Ac and construction of Neu5Ac(α2-8)Neu5Ac due to differential reactivity between 2-chloro and 2-fluoro-Neu5Ac, we realized an efficient total synthesis of GD3.