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

Base Information

• Chemical Name: 1-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-D-glycero-D-gulo-heptitol
• CAS No.: 1393360-77-4
• Molecular Formula: C₂₄H₂₈O₈
• Molecular Weight: 444.482
• Mol file: 1393360-77-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about 1-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-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:

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) → 1-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-D-glycero-D-gulo-heptitol (1393360-77-4)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tet.2012.04.001

Reference yield:

3-O-benzyl-4,6-O-p-methoxybenzylidene-D-glucopyranose → 1-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-D-glycero-D-gulo-heptitol (1393360-77-4)

Guidance literature:

Multi-step reaction with 3 steps

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

2.1: dicobalt octacarbonyl / 0.5 h / 20 °C

2.2: 48 h / 50 °C

3.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

With pyridine; dicobalt octacarbonyl; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2012.04.001

Reference yield:

benzyl bromide (100-39-0) → 1-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-D-glycero-D-gulo-heptitol (1393360-77-4)

Guidance literature:

Multi-step reaction with 6 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

6.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

With pyridine; dicobalt octacarbonyl; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2012.04.001

upstream raw materials:

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

benzyl bromide

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

Downstream raw materials:

3-O-benzyl-1,6-O-diacetyl-2-O-(p-methoxybenzyl)-4-O-tert-butyldiphenylsilyl-α-L-glucopyranose

3-O-benzyl-1,6-O-diacetyl-2-O-(p-methoxybenzyl)-4-O-tert-butyldiphenylsilyl-β-L-glucopyranose

3-O-benzyl-1,4-O-diacetyl-2-O-(p-methoxybenzyl)-β-L-galactopyranose

3-O-benzyl-1,6-O-diacetyl-2-O-(p-methoxybenzyl)-β-L-galactopyranose