2-(trimethylsilyl)ethyl 2-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 2-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 281658-15-9
• Molecular Formula: C₅₅H₆₃NO₁₃Si
• Molecular Weight: 974.19
• Mol file: 281658-15-9.mol

Synonyms:2-(trimethylsilyl)ethyl 2-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property of 2-(trimethylsilyl)ethyl 2-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(trimethylsilyl)ethyl 2-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 10 articles about 2-(trimethylsilyl)ethyl 2-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 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: 68.0%

2-(trimethylsilyl)ethyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (281658-14-8) → 2-(trimethylsilyl)ethyl 2-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (281658-15-9)

Guidance literature:

With hydrogenchloride; MS 3 Angstroem; sodium cyanoborohydride; In tetrahydrofuran; at 0 ℃; for 0.0833333h;

DOI:10.1016/S0008-6215(00)00011-2

Reference yield:

benzyl bromide (100-39-0) → 2-(trimethylsilyl)ethyl 2-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (281658-15-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Bu₂SnO / benzene / 6 h / Heating

1.2: 81 percent / Bu₄NBr / benzene / 65 °C

2.1: 98.5 percent / pyridine / 3 h / 20 °C

3.1: 90 percent / MS 4 Angstroem; N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / 18 h / 20 °C

4.1: 68 percent / NaBH₃CN; MS 3 Angstroem; HCl in ether / tetrahydrofuran / 0.08 h / 0 °C

With hydrogenchloride; N-iodo-succinimide; trifluorormethanesulfonic acid; MS 3 Angstroem; MS 4 Angstroem; di(n-butyl)tin oxide; sodium cyanoborohydride; In tetrahydrofuran; pyridine; dichloromethane; benzene; 1.1: stannylation / 1.2: benzylation / 2.1: Acetylation / 3.1: glycosylation / 4.1: Reduction;

DOI:10.1016/S0008-6215(00)00011-2

Reference yield:

ethyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside (173935-67-6) → 2-(trimethylsilyl)ethyl 2-O-acetyl-3,6-di-O-benzyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (281658-15-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 98.5 percent / pyridine / 3 h / 20 °C

2: 90 percent / MS 4 Angstroem; N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / 18 h / 20 °C

3: 68 percent / NaBH₃CN; MS 3 Angstroem; HCl in ether / tetrahydrofuran / 0.08 h / 0 °C

With hydrogenchloride; N-iodo-succinimide; trifluorormethanesulfonic acid; MS 3 Angstroem; MS 4 Angstroem; sodium cyanoborohydride; In tetrahydrofuran; pyridine; dichloromethane; 1: Acetylation / 2: glycosylation / 3: Reduction;

DOI:10.1016/S0008-6215(00)00011-2

upstream raw materials:

2-(trimethylsilyl)ethyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

benzyl bromide

S-ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

ethyl 3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside