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

Base Information

• Chemical Name: octyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-mannospyranoside
• CAS No.: 300343-34-4
• Molecular Formula: C₅₅H₆₆O₁₂
• Molecular Weight: 919.122
• Mol file: 300343-34-4.mol

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

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

There total 4 articles about octyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-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: 82.0%

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) → octyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-mannospyranoside (300343-34-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

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

Reference yield:

ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside (125411-99-6) → octyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-mannospyranoside (300343-34-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 48 percent / tetramethylurea; silver trifluoromethanesulfonate; Br₂ / 3 Angstroem molecular sieves / toluene / 4.5 h

2: 90 percent / HF-pyridine / CH₂Cl₂ / 0.75 h / 20 °C

3: 82 percent / Bu₄NF / tetrahydrofuran / 1 h / 20 °C

With tetrabutyl ammonium fluoride; bromine; silver trifluoromethanesulfonate; pyridine hydrogenfluoride; tetramethylurea; 3 A molecular sieve; In tetrahydrofuran; dichloromethane; toluene; 1: Condensation / 2: Fluorination / 3: Elimination;

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

Reference yield:

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)-α-D-mannospyranoside (300343-34-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 48 percent / tetramethylurea; silver trifluoromethanesulfonate; Br₂ / 3 Angstroem molecular sieves / toluene / 4.5 h

2: 90 percent / HF-pyridine / CH₂Cl₂ / 0.75 h / 20 °C

3: 82 percent / Bu₄NF / tetrahydrofuran / 1 h / 20 °C

With tetrabutyl ammonium fluoride; bromine; silver trifluoromethanesulfonate; pyridine hydrogenfluoride; tetramethylurea; 3 A molecular sieve; In tetrahydrofuran; dichloromethane; toluene; 1: Condensation / 2: Fluorination / 3: Elimination;

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

upstream 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

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

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