133411-35-5

Basic information

• Product Name: 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)-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside
• Synonyms: 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)-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside
• CAS NO: 133411-35-5
• Molecular Weight: 1220.37
• Mol File: 133411-35-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 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)-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 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)-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside(133411-35-5)
• EPA Substance Registry System: 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)-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside(133411-35-5)

Safety Data

• Hazardous Substances Data: 133411-35-5(Hazardous Substances Data)

Upstream product

• 3282-30-2 pivaloyl chloride 
• 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 
• 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 articles and documents

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.

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).