213459-83-7

Basic information

• Product Name: 2-[(2S,3R,4R,5R,6R)-6-Benzyloxymethyl-2-ethylsulfanyl-4,5-bis-(isopropyl-dimethyl-silanyloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
• Synonyms: 2-[(2S,3R,4R,5R,6R)-6-Benzyloxymethyl-2-ethylsulfanyl-4,5-bis-(isopropyl-dimethyl-silanyloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
• CAS NO: 213459-83-7
• Molecular Weight: 643.992
• Mol File: 213459-83-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-[(2S,3R,4R,5R,6R)-6-Benzyloxymethyl-2-ethylsulfanyl-4,5-bis-(isopropyl-dimethyl-silanyloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(2S,3R,4R,5R,6R)-6-Benzyloxymethyl-2-ethylsulfanyl-4,5-bis-(isopropyl-dimethyl-silanyloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione(213459-83-7)
• EPA Substance Registry System: 2-[(2S,3R,4R,5R,6R)-6-Benzyloxymethyl-2-ethylsulfanyl-4,5-bis-(isopropyl-dimethyl-silanyloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione(213459-83-7)

Safety Data

• Hazardous Substances Data: 213459-83-7(Hazardous Substances Data)

Upstream product

• 3634-56-8 isopropyldimethylsilyl chloride 
• 169048-88-8 ethyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 129519-28-4 2-((6S,7R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione 

Downstream Products

• 213459-92-8 Acetic acid (2R,3S,4S,5R,6S)-6-(5-azido-pentyloxy)-5-benzyloxy-2-benzyloxymethyl-4-[(2S,3R,4R,5S,6R)-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-yl ester 
• 213459-90-6 C₅₈H₇₈N₄O₁₃Si₂ 

Relevant articles and documents

Synthesis of the spacer-containing β-D-GalpNAc-(1 →4)-β-D-GlcpNAc-(1→3)-α-D-Galp moiety, representing the non-fucosylated backbone trisaccharide of the glycocalyx glycan of the parasite Schistosoma mansoni

The chemical synthesis of β-D-GalpNAc-(1→4)-β-D-GlcpNAc-(1→3)-α-D-Galp-(1→O)-(CH2)5NH2 is described. This structure represents the nonfucosylated backbone trisaccharide of the glycocalyx glycan of the cercarial stage of the parasite Schistosoma mansoni. Synthesis of the trisaccharide was achieved via a stepwise coupling approach. 5-Azidopentyl 4-O-acetyl-2,6-di-O-benzyl-α-D-galactopyranoside was condensed with ethyl 6-O-benzyl-2-deoxy-3,4-di-O-dimethylisopropylsilyl-2-phthalimido- 1-thio-β-D-glucopyranoside, using N-iodosuccinimide and silver trifluoromethanesulfonate as a catalyst system, followed by the removal of the silyl ether groups to afford a disaccharide acceptor. Coupling of ethyl 4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2- phthalimido-1-thio-β-D-galactopyranoside to the disaccharide acceptor, using methylsulfenyl bromide and silver trifluoromethanesulfonate as a catalyst system, gave a protected trisaccharide. Deprotection of this compound yielded the target structure.