5,16,27-tris(benzyloxy)-32-amino-4,12,15,23,26-pentaoxo-5,11,16,22,27-pentaazadotriacontanoic acid

Base Information

• Chemical Name: 5,16,27-tris(benzyloxy)-32-amino-4,12,15,23,26-pentaoxo-5,11,16,22,27-pentaazadotriacontanoic acid
• CAS No.: 130946-43-9
• Molecular Formula: C₄₈H₆₈N₆O₁₀
• Molecular Weight: 889.102
• Mol file: 130946-43-9.mol

Synonyms:5,16,27-tris(benzyloxy)-32-amino-4,12,15,23,26-pentaoxo-5,11,16,22,27-pentaazadotriacontanoic acid

Chemical Property of 5,16,27-tris(benzyloxy)-32-amino-4,12,15,23,26-pentaoxo-5,11,16,22,27-pentaazadotriacontanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5,16,27-tris(benzyloxy)-32-amino-4,12,15,23,26-pentaoxo-5,11,16,22,27-pentaazadotriacontanoic acid

There total 16 articles about 5,16,27-tris(benzyloxy)-32-amino-4,12,15,23,26-pentaoxo-5,11,16,22,27-pentaazadotriacontanoic acid 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: 21.0%

5,16,27-tris(benzyloxy)-31-cyano-4,12,15,23,26-pentaoxo-5,11,16,22,27-pentaazahentriacontanoic acid (130946-42-8) → 5,16,27-tris(benzyloxy)-32-amino-4,12,15,23,26-pentaoxo-5,11,16,22,27-pentaazadotriacontanoic acid (130946-43-9)

Guidance literature:

With ammonium hydroxide; hydrogen; Raney nickel W-2; In methanol; at 0 ℃; for 3h; under 2947.7 - 3102.9 Torr;

DOI:10.1016/S0040-4020(01)87913-8

Reference yield:

O-benzyl-N-(5-aminopentyl)-N-(tert-butoxycarbonyl)hydroxylamine (129245-21-2) → 5,16,27-tris(benzyloxy)-32-amino-4,12,15,23,26-pentaoxo-5,11,16,22,27-pentaazadotriacontanoic acid (130946-43-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 44 percent / DCC, DMAP / CH₂Cl₂ / 96 h / 0 deg C to r.t.

2: 2.46 g / TFA / CH₂Cl₂ / 1) 3 min, 0 deg C, 2) 17 min, without cooling

3: 78 percent / pyridine / 1.87 h / 101 °C

4: 21 percent / H₂, NH₃, conc.NH₄OH / Raney nickel W-2 / methanol / 3 h / 0 °C / 2947.7 - 3102.9 Torr

With pyridine; dmap; ammonium hydroxide; hydrogen; dicyclohexyl-carbodiimide; trifluoroacetic acid; Raney nickel W-2; In methanol; dichloromethane;

DOI:10.1016/S0040-4020(01)87913-8

Reference yield:

5,16-bis(benzyloxy)-20-cyano-4,12,15-trioxo-5,11,16-triazaeicosanoic acid (129245-24-5) → 5,16,27-tris(benzyloxy)-32-amino-4,12,15,23,26-pentaoxo-5,11,16,22,27-pentaazadotriacontanoic acid (130946-43-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 44 percent / DCC, DMAP / CH₂Cl₂ / 96 h / 0 deg C to r.t.

2: 2.46 g / TFA / CH₂Cl₂ / 1) 3 min, 0 deg C, 2) 17 min, without cooling

3: 78 percent / pyridine / 1.87 h / 101 °C

4: 21 percent / H₂, NH₃, conc.NH₄OH / Raney nickel W-2 / methanol / 3 h / 0 °C / 2947.7 - 3102.9 Torr

With pyridine; dmap; ammonium hydroxide; hydrogen; dicyclohexyl-carbodiimide; trifluoroacetic acid; Raney nickel W-2; In methanol; dichloromethane;

DOI:10.1016/S0040-4020(01)87913-8

upstream raw materials:

5,16,27-tris(benzyloxy)-31-cyano-4,12,15,23,26-pentaoxo-5,11,16,22,27-pentaazahentriacontanoic acid

O-benzyl-N-(5-aminopentyl)-N-(tert-butoxycarbonyl)hydroxylamine

5,16-bis(benzyloxy)-20-cyano-4,12,15-trioxo-5,11,16-triazaeicosanoic acid

27--6,17-bis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22-tetraazaheptacosanenitrile

Downstream raw materials:

1,12,23-tris(benzyloxy)-1,6,12,17,23,28-hexaazacyclotritriacontane-2,5,13,16,24,27-hexone

nocardamine

Refernces

• 1、 Bergeron, R. J.,McManis, J. S.. "THE TOTAL SYNTHESIS OF DESFERRIOXAMINES E AND G". . p. 5881 - 5888. Retrieved 2007/10/02.