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

Base Information

• Chemical Name: 1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-2-heptulopyranose
• CAS No.: 191097-59-3
• Molecular Formula: C₄₂H₄₂N₂O₆
• Molecular Weight: 670.805

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

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

Chemical Property:

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

There total 1 articles about 1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-2-heptulopyranose 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: 76.0%

2-Methyl-1H-benzimidazole (615-15-6) + (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → 1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-2-heptulopyranose (191097-59-3)

Guidance literature:

2-Methyl-1H-benzimidazole; With n-butyllithium; In tetrahydrofuran; hexane; for 1h;

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; hexane; at -85 ℃; for 1h;

DOI:10.1080/07328309708006530

Reference yield: 92.0%

acetyl chloride (75-36-5) + 1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-2-heptulopyranose (191097-59-3) → 2-O-Acetyl-1-[2-(1-acetyl)-benzimidazolyl]-3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-2-heptulopyranose (191097-68-4)

Guidance literature:

With triethylamine; In dichloromethane; for 0.166667h;

DOI:10.1080/07328309708006530

Reference yield: 47.0%

(2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid (120444-48-6) + 1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-2-heptulopyranose (191097-59-3) → 1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-2-heptulopyranosyl(methyl-2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

Guidance literature:

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; for 1h;

DOI:10.1080/07328309708006530

upstream raw materials:

2-Methyl-1H-benzimidazole

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

Downstream raw materials:

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

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

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

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

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