3-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-1-O-triethylsilyl-D-glycero-D-gulo-heptitol

Base Information

• Chemical Name: 3-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-1-O-triethylsilyl-D-glycero-D-gulo-heptitol
• CAS No.: 1393360-75-2
• Molecular Formula: C₃₀H₄₂O₈Si
• Molecular Weight: 558.744
• Mol file: 1393360-75-2.mol

Synonyms:3-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-1-O-triethylsilyl-D-glycero-D-gulo-heptitol

Chemical Property of 3-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-1-O-triethylsilyl-D-glycero-D-gulo-heptitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-1-O-triethylsilyl-D-glycero-D-gulo-heptitol

There total 6 articles about 3-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-1-O-triethylsilyl-D-glycero-D-gulo-heptitol 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: 55.0%

triethylsilane (617-86-7) + carbon monoxide (201230-82-2) + 3-O-benzyl-1,2-O-diacetyl-4,6-O-p-methoxybenzylidene-D-glucopyranose (1404561-47-2) → 3-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-1-O-triethylsilyl-D-glycero-D-gulo-heptitol (1393360-75-2) + 4-O-acetyl-3,7-anhydro-5-O-benzyl-1,2-O-ditriethylsilyl-6,8-O-p-methoxybenzylidene-D-glycero-D-gulo-oct-1-enitol (1393360-91-2)

Guidance literature:

triethylsilane; carbon monoxide; With dicobalt octacarbonyl; at 20 ℃; for 0.5h;

3-O-benzyl-1,2-O-diacetyl-4,6-O-p-methoxybenzylidene-D-glucopyranose; In benzene; at 50 ℃; for 48h;

DOI:10.1016/j.tet.2012.04.001

Reference yield:

3-O-benzyl-4,6-O-p-methoxybenzylidene-D-glucopyranose → 3-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-1-O-triethylsilyl-D-glycero-D-gulo-heptitol (1393360-75-2) + 4-O-acetyl-3,7-anhydro-5-O-benzyl-1,2-O-ditriethylsilyl-6,8-O-p-methoxybenzylidene-D-glycero-D-gulo-oct-1-enitol (1393360-91-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine / dichloromethane / 20 °C / Inert atmosphere

2.1: dicobalt octacarbonyl / 0.5 h / 20 °C

2.2: 48 h / 50 °C

With pyridine; dicobalt octacarbonyl; In dichloromethane;

DOI:10.1016/j.tet.2012.04.001

Reference yield:

benzyl bromide (100-39-0) → 3-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-1-O-triethylsilyl-D-glycero-D-gulo-heptitol (1393360-75-2) + 4-O-acetyl-3,7-anhydro-5-O-benzyl-1,2-O-ditriethylsilyl-6,8-O-p-methoxybenzylidene-D-glycero-D-gulo-oct-1-enitol (1393360-91-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / tetrahydrofuran / 50 °C

2.1: ion exchange resin (H⁺ form) / water / 70 °C

3.1: N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere

4.1: pyridine / dichloromethane / 20 °C / Inert atmosphere

5.1: dicobalt octacarbonyl / 0.5 h / 20 °C

5.2: 48 h / 50 °C

With pyridine; dicobalt octacarbonyl; sodium hydride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2012.04.001

upstream raw materials:

triethylsilane

carbon monoxide

3-O-benzyl-1,2-O-diacetyl-4,6-O-p-methoxybenzylidene-D-glucopyranose

3-O-benzyl-D-glucopyranose

Downstream raw materials:

3-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-D-glycero-D-gulo-heptitol

1-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-D-glycero-D-gulo-heptitol

3-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-1-O-tert-butyldiphenylsilyl-D-glycero-D-gulo-heptitol

1-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-3-O-tert-butyldiphenylsilyl-D-glycero-D-gulo-heptitol