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

Base Information

• Chemical 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
• CAS No.: 300343-32-2
• Molecular Formula: C₆₇H₉₂O₁₃Si₂
• Molecular Weight: 1161.63
• Mol file: 300343-32-2.mol

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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 1 articles about 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 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 48.0%

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

Guidance literature:

With bromine; silver trifluoromethanesulfonate; tetramethylurea; 3 A molecular sieve; In toluene; for 4.5h;

DOI:10.1016/S0008-6215(00)00071-9

Reference yield: 90.0%

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) → 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 (300343-33-3)

Guidance literature:

With pyridine hydrogenfluoride; In dichloromethane; at 20 ℃; for 0.75h;

DOI:10.1016/S0008-6215(00)00071-9

Reference yield:

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) → (2R,3R,4S,5S,6S)-2-Hydroxymethyl-6-octyloxy-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3,5-diol

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / HF-pyridine / CH₂Cl₂ / 0.75 h / 20 °C

2: 82 percent / Bu₄NF / tetrahydrofuran / 1 h / 20 °C

3: NaOMe / methanol / 96 h

With tetrabutyl ammonium fluoride; sodium methylate; pyridine hydrogenfluoride; In tetrahydrofuran; methanol; dichloromethane; 1: Fluorination / 2: Elimination / 3: Elimination;

DOI:10.1016/S0008-6215(00)00071-9

upstream raw materials:

ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside

octyl 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-α-D-mannopyranoside

Downstream raw materials:

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

octyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-mannospyranoside

Refernces