164525-86-4

Basic information

• Product Name: 2-(trimethylsilyl)ethyl <2,3-bis-O-(phenylmethyl)-β-D-galactopyranosyl>-(1,4)-2,3,6-tris-O-(phenylmethyl)-β-D-glucopyranoside
• Synonyms: 2-(trimethylsilyl)ethyl <2,3-bis-O-(phenylmethyl)-β-D-galactopyranosyl>-(1,4)-2,3,6-tris-O-(phenylmethyl)-β-D-glucopyranoside
• CAS NO: 164525-86-4
• Molecular Weight: 893.159
• Mol File: 164525-86-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-(trimethylsilyl)ethyl <2,3-bis-O-(phenylmethyl)-β-D-galactopyranosyl>-(1,4)-2,3,6-tris-O-(phenylmethyl)-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(trimethylsilyl)ethyl <2,3-bis-O-(phenylmethyl)-β-D-galactopyranosyl>-(1,4)-2,3,6-tris-O-(phenylmethyl)-β-D-glucopyranoside(164525-86-4)
• EPA Substance Registry System: 2-(trimethylsilyl)ethyl <2,3-bis-O-(phenylmethyl)-β-D-galactopyranosyl>-(1,4)-2,3,6-tris-O-(phenylmethyl)-β-D-glucopyranoside(164525-86-4)

Safety Data

• Hazardous Substances Data: 164525-86-4(Hazardous Substances Data)

Upstream product

• 117253-25-5 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 117253-23-3 2-(trimethylsilyl)ethyl 4-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 115969-51-2 2-(trimethylsilyl)ethyl O-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside 

Relevant articles and documents

A practical method for the synthesis of sialyl α-glycosides

Addition of 2,4-dimethylbenzenesulfenyl chloride to sialic acid glycal gives crystalline 2-chloro-3-thiosialic acid 3 in 85% yield. Reaction of 3 with sodium thiomethoxide in acetonitrile at 0°C affords the sialic acid donor α-2-(methylthio)-3-thiosialic

SYNTHETIC STUDIES ON SIALOGLYCOCONJUGATES 65: STEREOCONTROLLED SYNTHESIS OF POSITIONAL ISOMERS OF TUMOR-ASSOCIATED GANGLIOSIDE ANTIGENS, SIALYL LEWIS X AND SIALYL PARAGLOBOSIDE

Stereocontrolled synthesis of neolacto series ganglioside analogs containing GlcNAcβ1-6Gal substituted for the GlcNAcβ1-3Gal residue in sialyl Lewis X and sialyl neolactotetraosyl ceramide is described.Tri- and tetra- saccharides 7 and 10 containing GlcNAcβ1->6Gal residue were obtained by glycosylation of 2-(trimethylsilyl)ethyl O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (2) with methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (4) for the synthesis of sialyl paragloboside or methyl O-(2,3,4- tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (6) for sialyl LeX synthesis.Compounds 7 and 10 were transformed via removal of the phthaloyl group followed by N-acetylation, O-acetylation and reductive ring-opening of the benzylidene acetal into the acceptors 9 and 12.Dimethyl (methylthio)sulfonium triflate (DMTST)-promoted coupling of 9 or 12 with methyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-2,4,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside (13) gave the desired pentasaccharide 14 and hexasaccharide 18, respectively, which were converted via reductive removal of the benzyl groups, O-acetylation, removal of the 2-(trimethylsilyl)ethyl group and treatment with trichloroacetonitrile, into the α-trichloroacetimidates 17 and 21.Condensation of 17 or 21 with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol (22) gave the β-glycosides 23 and 26, which were transformed via reduction of the azido group, coupling with octadecanoic acid, O-deacylation and saponification of the methyl ester group, into the desired positional isomers of sialyl neolactotetraosyl ceramide 25 and of sialyl LeX gangliosides 28, respectively.