N¹,N⁸-bis(2,3-dihydroxybenzoyl)-M⁴-(L-threonyl)spermidine hydrobromide

Base Information

• Chemical Name: N¹,N⁸-bis(2,3-dihydroxybenzoyl)-M⁴-(L-threonyl)spermidine hydrobromide
• CAS No.: 82247-46-9
• Molecular Formula: BrH*C₂₅H₃₄N₄O₈
• Molecular Weight: 599.479
• Mol file: 82247-46-9.mol

Synonyms:N¹,N⁸-bis(2,3-dihydroxybenzoyl)-M⁴-(L-threonyl)spermidine hydrobromide

Chemical Property of N¹,N⁸-bis(2,3-dihydroxybenzoyl)-M⁴-(L-threonyl)spermidine hydrobromide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N¹,N⁸-bis(2,3-dihydroxybenzoyl)-M⁴-(L-threonyl)spermidine hydrobromide

There total 4 articles about N¹,N⁸-bis(2,3-dihydroxybenzoyl)-M⁴-(L-threonyl)spermidine hydrobromide 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: 90.0%

N4-L-threonyl-N1,N8-bis(2,3-dimethoxybenzoyl)spermidine (89675-85-4) → N1,N8-bis(2,3-dihydroxybenzoyl)-M4-(L-threonyl)spermidine hydrobromide (82247-46-9)

Guidance literature:

With boron tribromide; In dichloromethane; for 12h; Ambient temperature;

DOI:10.1021/ja00323a004

Reference yield:

N1,N8-Bis(2,3-bis(methyloxy)benzoyl)spermidine (78217-75-1) → N1,N8-bis(2,3-dihydroxybenzoyl)-M4-(L-threonyl)spermidine hydrobromide (82247-46-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) N-hydroxysuccinimide, dicyclohexylcarbodiimide, Et₃N / 1) THF, 0 deg C

2: hydrogen, HCl / PdCl₂ / methanol / 24 h

3: 1.) BBr₃, 2.) H₂O / 1) CH₂Cl_2. 0 deg C, 6 h; 2) methanol

With hydrogenchloride; 1-hydroxy-pyrrolidine-2,5-dione; water; hydrogen; boron tribromide; triethylamine; dicyclohexyl-carbodiimide; palladium dichloride; In methanol;

DOI:10.1021/ja00380a032

Reference yield:

N4-(N-carbobenzoxy-L-threonyl)-N1,N8-bis(2,3-dimethoxybenzoyl)spermidine (82247-45-8) → N1,N8-bis(2,3-dihydroxybenzoyl)-M4-(L-threonyl)spermidine hydrobromide (82247-46-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen, HCl / PdCl₂ / methanol / 24 h

2: 1.) BBr₃, 2.) H₂O / 1) CH₂Cl_2. 0 deg C, 6 h; 2) methanol

With hydrogenchloride; water; hydrogen; boron tribromide; palladium dichloride; In methanol;

DOI:10.1021/ja00380a032

upstream raw materials:

N⁴-L-threonyl-N¹,N⁸-bis(2,3-dimethoxybenzoyl)spermidine

((1S,2R)-1-{[4-(2,3-Dimethoxy-benzoylamino)-butyl]-[3-(2,3-dimethoxy-benzoylamino)-propyl]-carbamoyl}-2-hydroxy-propyl)-carbamic acid tert-butyl ester

N¹,N⁸-Bis(2,3-bis(methyloxy)benzoyl)spermidine

N⁴-(N-carbobenzoxy-L-threonyl)-N¹,N⁸-bis(2,3-dimethoxybenzoyl)spermidine

Downstream raw materials:

parabactin azide

aminoparabactin

agrobactin

parabactin

Refernces

• 1、 Bergeron, Raymond J.,Kline, Steven J.. "Short Synthesis of Parabactin". . p. 4489 - 4492. Retrieved 2007/10/02.