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

Base Information

Chemical Name:acetyl-3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyl)benzimidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranoside
CAS No.:191097-77-5
Molecular Formula:C₅₁H₅₀N₂O₇
Molecular Weight:802.967
Hs Code.:

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

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

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

There total 7 articles about acetyl-3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyl)benzimidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranoside 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: 93.0%

: 506-96-7
Acetyl bromide

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

: 191097-77-5
acetyl-3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyl)benzimidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;
DOI:10.1080/07328309708006530

Reference yield:

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

: 191097-77-5
acetyl-3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyl)benzimidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranoside

Guidance literature:: Multi-step reaction with 3 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

3.1: 93 percent / sodium hydride / dimethylformamide / 0.5 h / 0 °C

With n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 1.1: benzylation / 2.1: Metallation / 2.2: Addition / 3.1: Acetylation;
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

: 191097-77-5
acetyl-3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyl)benzimidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranoside

Guidance literature:: Multi-step reaction with 3 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

3.1: 93 percent / sodium hydride / dimethylformamide / 0.5 h / 0 °C

With n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Addition / 2.1: benzylation / 3.1: Acetylation;
DOI:10.1080/07328309708006530