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

Base Information

Chemical Name:3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyl)benzimidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranose
CAS No.:191097-60-6
Molecular Formula:C₄₉H₄₈N₂O₆
Molecular Weight:760.93
Hs Code.:

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

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

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

There total 4 articles about 3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyl)benzimidazolyl]-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: 89.0%

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 5805-83-4
1-benzyl-2-methylbenzimidazole

: 191097-60-6
3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyl)benzimidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranose

Guidance literature:: 1-benzyl-2-methylbenzimidazole; With n-butyllithium; In tetrahydrofuran; hexane; at -80 ℃; for 0.333333h;

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; hexane; at -80 ℃; for 0.5h;
DOI:10.1080/07328309708006530

Reference yield:

: 615-15-6
2-Methyl-1H-benzimidazole

: 191097-60-6
3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyl)benzimidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranose

Guidance literature:: Multi-step reaction with 2 steps

1.1: 90 percent / sodium hydride / dimethylformamide / 0.25 h / 0 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -80 °C

2.2: 89 percent / tetrahydrofuran; hexane / 0.5 h / -80 °C

With n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 1.1: benzylation / 2.1: Metallation / 2.2: Addition;
DOI:10.1080/07328309708006530

Reference yield:

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 191097-60-6
3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyl)benzimidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranose

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: 61 percent / sodium hydride / dimethylformamide / 0.25 h

With n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Addition / 2.1: benzylation;
DOI:10.1080/07328309708006530