methyl (N-benzyloxycarbonyl-2-aminoethyl 4-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-2-O-pivaloyl-α-L-idopyranoside)uronate

Base Information

• Chemical Name: methyl (N-benzyloxycarbonyl-2-aminoethyl 4-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-2-O-pivaloyl-α-L-idopyranoside)uronate
• CAS No.: 1364662-68-9
• Molecular Formula: C₄₄H₅₄N₄O₁₅
• Molecular Weight: 878.931
• Mol file: 1364662-68-9.mol

Synonyms:methyl (N-benzyloxycarbonyl-2-aminoethyl 4-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-2-O-pivaloyl-α-L-idopyranoside)uronate

Chemical Property of methyl (N-benzyloxycarbonyl-2-aminoethyl 4-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-2-O-pivaloyl-α-L-idopyranoside)uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (N-benzyloxycarbonyl-2-aminoethyl 4-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-2-O-pivaloyl-α-L-idopyranoside)uronate

There total 7 articles about methyl (N-benzyloxycarbonyl-2-aminoethyl 4-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-2-O-pivaloyl-α-L-idopyranoside)uronate 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: 91.0%

methyl (N-benzyloxycarbonyl-2-aminoethyl 4-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl)-3-O-benzyl-2-O-pivaloyl-α-L-idopyranoside)uronate (1364662-67-8) → methyl (N-benzyloxycarbonyl-2-aminoethyl 4-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-2-O-pivaloyl-α-L-idopyranoside)uronate (1364662-68-9)

Guidance literature:

With pyridine; hydrazine hydrate; acetic acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1039/c2ob06607f

Reference yield:

C42H59N3O14Si → methyl (N-benzyloxycarbonyl-2-aminoethyl 4-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-2-O-pivaloyl-α-L-idopyranoside)uronate (1364662-68-9)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine; dmap / 36 h / 20 °C

2: pyridine hydrofluoride / tetrahydrofuran / 28 h / -15 - 20 °C / Inert atmosphere

3: potassium carbonate / dichloromethane / 6 h / 20 °C

4: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

5: pyridine; hydrazine hydrate; acetic acid / dichloromethane / 2 h / 20 °C

With pyridine; dmap; pyridine hydrofluoride; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; hydrazine hydrate; acetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c2ob06607f

Reference yield:

C47H67N3O15Si (1380592-26-6) → methyl (N-benzyloxycarbonyl-2-aminoethyl 4-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-2-O-pivaloyl-α-L-idopyranoside)uronate (1364662-68-9)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine hydrofluoride / tetrahydrofuran / 28 h / -15 - 20 °C / Inert atmosphere

2: potassium carbonate / dichloromethane / 6 h / 20 °C

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

4: pyridine; hydrazine hydrate; acetic acid / dichloromethane / 2 h / 20 °C

With pyridine; pyridine hydrofluoride; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; hydrazine hydrate; acetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c2ob06607f

upstream raw materials:

C₄₇H₆₇N₃O₁₅Si

O-(methyl 4-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl)-3-O-benzyl-2-O-pivaloyl-L-idopyranosuronate)trichloroacetimidate

methyl (N-benzyloxycarbonyl-2-aminoethyl 4-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl)-3-O-benzyl-2-O-pivaloyl-α-L-idopyranoside)uronate

methyl (dimethylthexylsilyl 3-O-benzyl-β-L-idopyranoside)uronate

Downstream raw materials:

N-benzyloxycarbonyl-2-aminoethyl-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)(1->4)-O-(methyl 3-O-benzyl-2-O-pivaloyl-α-L-idopyranosyluronate)(1->4)-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)(1->4)methyl 3-O-benzyl-2-O-pivaloyl-α-L-idopyranosiduronate

methyl 4-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl)-1,5-anhydro-3-O-benzyl-2-O-pivaloyl-L-xylo-hex-1-enitoluronate

N-benzyloxycarbonyl-2-aminoethyl(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl)(1->4)(methyl 3-O-benzyl-2-O-pivaloyl-α-L-idopyranosyluronate)(1->4)(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)(1->4)methyl 3-O-benzyl-2-O-pivaloyl-α-L-idopyranosiduronate

N-benzyloxycarbonyl-2-aminoethyl-4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-α-L-idopyranosiduronic acid