151651-16-0

Basic information

• Product Name: 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2-azido-6-O-benzyl-2-deoxy-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside
• Synonyms: 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2-azido-6-O-benzyl-2-deoxy-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside
• CAS NO: 151651-16-0
• Molecular Weight: 868.112
• Mol File: 151651-16-0.mol

Chemical Properties

• CAS DataBase Reference: 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2-azido-6-O-benzyl-2-deoxy-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2-azido-6-O-benzyl-2-deoxy-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside(151651-16-0)
• EPA Substance Registry System: 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2-azido-6-O-benzyl-2-deoxy-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside(151651-16-0)

Safety Data

• Hazardous Substances Data: 151651-16-0(Hazardous Substances Data)

Upstream product

• 67673-39-6 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide 
• 117253-05-1 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 151651-13-7 (2R,3R,4R,5R,6S)-5-Azido-6-[(2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-2-hydroxymethyl-tetrahydro-pyran-3,4-diol 
• 151651-11-5 Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-[(2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-4-yl ester 
• 100-39-0 benzyl bromide 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 139244-25-0 2-(trimethylsilyl)ethyl (2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 168139-39-7 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2-amino-6-O-benzyl-2-deoxy-3-O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyloyl-1''<*>2'-lactam)-β-D-galactopyranosyl>-β-D-glucopyranoside 
• 139244-26-1 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2-azido-6-O-benzyl-2-deoxy-3-O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylate)-β-D-galactopyranosyl>-β-D-glucopyranoside 

Relevant articles and documents

Synthesis of ganglioside lactams corresponding to GM1-, GM2-, GM3-, and GM4-ganglioside lactones

Ganglioside lactams are potentially useful analogs of ganglioside lactones, which are highly immunogenic derivatives of gangliosides. The lactam corresponding to the GM3-lactone saccharide has been synthesized by sialylation of a suitably protected lactose derivative carrying an azido group in the 2′-position, followed by reduction and ring closure to form GM3-lactam. Glycosylation in the 4-position of the central saccharide unit gave the GM2- and GM1-lactam saccharides. By a similar route, a 2-azido-Gal derivative was sialylated and treated as above to give the GM4-lactam saccharide. Deprotection gave the GM2-4-lactam saccharides in water soluble form, whereas attempted deprotection of the GM1-lactam caused its degradation. The GM3-lactam saccharide was coupled to ceramide, to afford the ganglioside lactam analog, and via a spacer to bovine serum albumin (BSA). The BSA conjugate was used as immunogen to raise monoclonal antibodies that cross-reacted with GM3-lactone. The antibodies were used in a histological staining of murine melanoma cells, clearly showing the presence of GM3-lactone on the cell surface. Keeping the GM2-4-lactam saccharides in D2O at 37 °C for 1 month caused marginal (0-11%) hydrolysis of the lactam ring.