N₅,N₁₀-diBoc-N₁₄-[4-((6-amino-2-(butylamino)-8-hydroxy-9H-purin-9-yl)methyl)-N-(2-amino-2-oxoethyl)benzamido]spermine

Base Information

• Chemical Name: N₅,N₁₀-diBoc-N₁₄-[4-((6-amino-2-(butylamino)-8-hydroxy-9H-purin-9-yl)methyl)-N-(2-amino-2-oxoethyl)benzamido]spermine
• CAS No.: 1623012-85-0
• Molecular Formula: C₃₉H₆₃N₁₁O₇
• Molecular Weight: 797.999
• Mol file: 1623012-85-0.mol

Synonyms:N₅,N₁₀-diBoc-N₁₄-[4-((6-amino-2-(butylamino)-8-hydroxy-9H-purin-9-yl)methyl)-N-(2-amino-2-oxoethyl)benzamido]spermine

Chemical Property of N₅,N₁₀-diBoc-N₁₄-[4-((6-amino-2-(butylamino)-8-hydroxy-9H-purin-9-yl)methyl)-N-(2-amino-2-oxoethyl)benzamido]spermine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N₅,N₁₀-diBoc-N₁₄-[4-((6-amino-2-(butylamino)-8-hydroxy-9H-purin-9-yl)methyl)-N-(2-amino-2-oxoethyl)benzamido]spermine

There total 11 articles about N₅,N₁₀-diBoc-N₁₄-[4-((6-amino-2-(butylamino)-8-hydroxy-9H-purin-9-yl)methyl)-N-(2-amino-2-oxoethyl)benzamido]spermine 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:

N1-benzylcarbamate-N5,N10-diBoc-N14-[4-((6-amino-2-(butylamino)-8-hydroxy-9H-purin-9-yl)methyl)-N-(2-amino-2-oxoethyl)benzamido]spermine (1623012-84-9) → N5,N10-diBoc-N14-[4-((6-amino-2-(butylamino)-8-hydroxy-9H-purin-9-yl)methyl)-N-(2-amino-2-oxoethyl)benzamido]spermine (1623012-85-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; at 20 ℃;

Reference yield:

methyl 4-((6-amino-8-bromo-2-(butylamino)-9H-purin-9-yl)methyl)benzoate → N5,N10-diBoc-N14-[4-((6-amino-2-(butylamino)-8-hydroxy-9H-purin-9-yl)methyl)-N-(2-amino-2-oxoethyl)benzamido]spermine (1623012-85-0)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium hydroxide / water; methanol / 18 h / Reflux

2: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; 4-methyl-morpholine / N,N-dimethyl-formamide

3: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran / 760.05 Torr

4: 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C

5: hydrogenchloride / 1,4-dioxane / 20 °C

6: sodium acetate / N,N-dimethyl-formamide / 2 h / 0 °C

7: triethylamine / N,N-dimethyl-formamide / 20 °C

8: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran / 20 °C

With 4-methyl-morpholine; hydrogenchloride; 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; palladium 10% on activated carbon; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; sodium acetate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;

Reference yield:

(2-(4-((6-amino-2-(butylamino)-8-hydroxy-9H-purin-9-yl)methyl)benzamido)acetic acid) (1510712-69-2) → N5,N10-diBoc-N14-[4-((6-amino-2-(butylamino)-8-hydroxy-9H-purin-9-yl)methyl)-N-(2-amino-2-oxoethyl)benzamido]spermine (1623012-85-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C

2: hydrogenchloride / 1,4-dioxane / 20 °C

3: sodium acetate / N,N-dimethyl-formamide / 2 h / 0 °C

4: triethylamine / N,N-dimethyl-formamide / 20 °C

5: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran / 20 °C

With hydrogenchloride; 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; palladium 10% on activated carbon; hydrogen; sodium acetate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide;

upstream raw materials:

2-chloroadenine

6-amino-2-butylamino-9H-purine

(2-(4-((6-amino-2-(butylamino)-8-hydroxy-9H-purin-9-yl)methyl)benzamido)acetic acid)

N₁,N₅,N₁₀-triBoc-N₁₄-[4-((6-amino-2-(butylamino)-8-hydroxy-9H-purin-9-yl)methyl)-N-(2-amino-2-oxoethyl)benzamido]spermine

Downstream raw materials:

(20R)-1-(4-((6-amino-2-(butylamino)-8-hydroxy-9H-purin-9-yl)methyl)phenyl)-9, 14-bis (tert-butoxycarbonyl)-20-(tert-butoxycarbonylamino)-1,4,19-trioxo-22-thia-2,5,9,14,18-pentaazapentacosane-24,25-diyl dipalmitate

Refernces

• 1、 -. "Conjugated TLR7 and/or TLR8 and TLR2 polycationic agonists". . . Retrieved 2014/09/03.