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

Base Information

• Chemical Name: 3,4,5,7-tetra-O-benzyl-1-deoxy-1-[2-(1-methyloxycarbonyl)benzimidazolyl]-α-D-gluco-2-heptulopyranose
• CAS No.: 191097-71-9
• Molecular Formula: C₄₄H₄₄N₂O₈
• Molecular Weight: 728.842

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

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

Chemical Property:

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

There total 2 articles about 3,4,5,7-tetra-O-benzyl-1-deoxy-1-[2-(1-methyloxycarbonyl)benzimidazolyl]-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:

2-Methyl-1H-benzimidazole (615-15-6) → 3,4,5,7-tetra-O-benzyl-1-deoxy-1-[2-(1-methyloxycarbonyl)benzimidazolyl]-α-D-gluco-2-heptulopyranose (191097-71-9)

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: 78 percent / triethylamine / CH₂Cl₂ / 0.33 h

With n-butyllithium; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Metallation / 1.2: Addition / 2.1: alkoxycarbonylation;

DOI:10.1080/07328309708006530

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → 3,4,5,7-tetra-O-benzyl-1-deoxy-1-[2-(1-methyloxycarbonyl)benzimidazolyl]-α-D-gluco-2-heptulopyranose (191097-71-9)

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: 78 percent / triethylamine / CH₂Cl₂ / 0.33 h

With n-butyllithium; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Metallation / 1.2: Addition / 2.1: alkoxycarbonylation;

DOI:10.1080/07328309708006530

Reference yield: 80.0%

3,4,5,7-tetra-O-benzyl-1-deoxy-1-[2-(1-methyloxycarbonyl)benzimidazolyl]-α-D-gluco-2-heptulopyranose (191097-71-9) → 1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-methyloxycarbonyl-α-D-gluco-2-heptulopyranose (191097-73-1)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 2h;

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:

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

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