300343-32-2

Basic information

• Product Name: octyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-mannospyranoside
• Synonyms: octyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-mannospyranoside
• CAS NO: 300343-32-2
• Molecular Weight: 1161.63
• Mol File: 300343-32-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: octyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-mannospyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: octyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-mannospyranoside(300343-32-2)
• EPA Substance Registry System: octyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-mannospyranoside(300343-32-2)

Safety Data

• Hazardous Substances Data: 300343-32-2(Hazardous Substances Data)

Upstream product

• 125411-99-6 ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 187139-97-5 octyl 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-mannopyranoside 

Downstream Products

• 300343-34-4 octyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-mannospyranoside 
• 300343-33-3 octyl 2-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-mannospyranoside 

Relevant articles and documents

Synthesis of α-galactosylated fragments related to the core-structure of the GPI anchor of Trypanosoma brucei

A series of octyl glycosides di- to tetrasaccharides related to the GPI anchor of Trypanosoma brucei was prepared. Treatment of octyl 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-mannopyranoside with ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside under activation with bromine and silver trifluoromethanesulfonate afforded the α-linked disaccharide octyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-mannospyranoside, the siloxane ring of which was regioselectively opened with a HF-pyridine complex to give the disaccharide acceptor octyl 3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-O-benzoyl-4-O-(3-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-α-D-mannopyranoside (4). Mannosylation of 4 with benzobromomannose (7), followed by fluoride catalyzed desilylation gave the trisaccharide octyl 2-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-mannospyranoside, which was deblocked via the deacylated intermediate octyl 3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-6-O-(α-D-mannopyranosyl)-α-D-mannospyranoside to afford the octyl glycoside trisaccharide octyl 3-O-(α-D-galactopyranosyl)-6-O-(α-D-mannopyranosyl)-α-D-mannospyranoside. Glycosylation of 4 with 3,4,6-tri-O-acetyl-2-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl trichloroacetimidate resulted in the tetrasaccharide octyl 2-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-6-O-[2-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]-α-D-mannospyranoside, sequential desilylation, deacylation and debenzylation, respectively, of which via the intermediate octyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-6-O-[2-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl]-α-D-mannospyranoside afforded the octyl glycoside tetrasaccharide octyl 3-O-(α-D-galactopyranosyl)-6-O-[2-O-(α-D-mannopyranosyl)-α-D-mannopyranosyl]-α-D-mannospyranoside. Copyright (C) 2000 Elsevier Science Ltd.