2,6-anhydro-1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol

Base Information

• Chemical Name: 2,6-anhydro-1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol
• CAS No.: 191097-75-3
• Molecular Formula: C₄₂H₄₀N₂O₅
• Molecular Weight: 652.79

Synonyms:2,6-anhydro-1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol

Chemical Property of 2,6-anhydro-1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol

Chemical Property:

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Technology Process of 2,6-anhydro-1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol

There total 4 articles about 2,6-anhydro-1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol 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: 35.0%

1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-2-heptulopyranose (191097-59-3) → 2,6-anhydro-1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol (191097-75-3)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 80 ℃; for 2h;

DOI:10.1080/07328309708006530

Reference yield: 20.1%

1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-2-heptulopyranose (191097-59-3) → 2,6-anhydro-1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol (191097-75-3) + 2,6-anhydro-1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol

Guidance literature:

With zinc(II) chloride; In dichloromethane; toluene; at 100 ℃; for 2h;

DOI:10.1080/07328309708006530

Reference yield:

2-Methyl-1H-benzimidazole (615-15-6) → 2,6-anhydro-1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol (191097-75-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h

1.2: 76 percent / tetrahydrofuran; hexane / 1 h / -85 °C

2.1: 35 percent / p-toluenesulphonic acid monohydrate / toluene / 2 h / 80 °C

With n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; toluene; 1.1: Metallation / 1.2: Addition / 2.1: Dehydration;

DOI:10.1080/07328309708006530

upstream raw materials:

1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-2-heptulopyranose

2-Methyl-1H-benzimidazole

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Downstream raw materials:

1,3,4,5-tetra-O-acetyl-7-[2-(1-acetyl)benzimidazolyl]-2,6-anhydro-7-deoxy-L-glycero-L-gulo-heptitol

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