3,5-dimethoxy-4-hydroxybenzoic acid-4-(N,N'-diBoc-guanidino)butyl ester

Base Information

• Chemical Name: 3,5-dimethoxy-4-hydroxybenzoic acid-4-(N,N'-diBoc-guanidino)butyl ester
• CAS No.: 1260119-24-1
• Molecular Formula: C₂₄H₃₇N₃O₉
• Molecular Weight: 511.572
• Mol file: 1260119-24-1.mol

Synonyms:3,5-dimethoxy-4-hydroxybenzoic acid-4-(N,N'-diBoc-guanidino)butyl ester

Chemical Property of 3,5-dimethoxy-4-hydroxybenzoic acid-4-(N,N'-diBoc-guanidino)butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-dimethoxy-4-hydroxybenzoic acid-4-(N,N'-diBoc-guanidino)butyl ester

There total 7 articles about 3,5-dimethoxy-4-hydroxybenzoic acid-4-(N,N'-diBoc-guanidino)butyl ester 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: 100.0%

3,5-dimethoxy-4-acetoxybenzoic acid 4-(N,N′-tert-butylcarbonylguanidino)butyl ester (1260119-23-0) → 3,5-dimethoxy-4-hydroxybenzoic acid-4-(N,N'-diBoc-guanidino)butyl ester (1260119-24-1)

Guidance literature:

With sodium methylate; In dichloromethane;

Reference yield: 30.0%

Leonuramin (18780-70-6) + N,N'-bis-Boc-S-methyl-isothiourea (322474-21-5) → Leonurine (24697-74-3,7097-09-8) + 3,5-dimethoxy-4-hydroxybenzoic acid-4-(N,N'-diBoc-guanidino)butyl ester (1260119-24-1)

Guidance literature:

In N,N-dimethyl-formamide; at 60 ℃;

DOI:10.1016/j.ejmech.2011.05.073

Reference yield:

3,5-dimethoxy-4-hydroxybenzoic acid (530-57-4) → 3,5-dimethoxy-4-hydroxybenzoic acid-4-(N,N'-diBoc-guanidino)butyl ester (1260119-24-1)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 2 h / 20 °C

2: 4-(dimethylamino)pyridinium tosylate; diisopropyl-carbodiimide / dichloromethane / 5 h / 20 °C

3: sodium methylate / methanol; dichloromethane / 1 h / 4 - 20 °C

With sodium methylate; triethylamine; 4-(dimethylamino)pyridinium tosylate; diisopropyl-carbodiimide; In methanol; dichloromethane;

DOI:10.1016/j.ejmech.2011.05.073

upstream raw materials:

3,5-dimethoxy-4-acetoxybenzoic acid 4-(N,N′-tert-butylcarbonylguanidino)butyl ester

di-tert-butyl dicarbonate

3,5-dimethoxy-4-hydroxybenzoic acid

Leonuramin

Downstream raw materials:

(R)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)butyl 4-((2-((tert-butoxycarbonyl)amino)-3-(prop-2-yn-1-ylthio)propanoyl)oxy)-3,5-dimethoxybenzoate

C₅₄H₈₀N₆O₂₀S₂

C₃₄H₄₈N₆O₁₂S₂

3,5-dimethoxy-4-(2-(N-Boc-amide)-3-allylsulfanyl-propionyl)-benzoic acid 4-(N,N'-Boc-guanidino)-butyl ester

Refernces

• 1、 Hou, Chenhui,Jiang, Qihui,Li, Feng,Li, Wenbao,Pang, Tao,Zhang, Liang,Zhu, Sifeng. "Novel Stachydrine-Leonurine Conjugate SL06 as a Potent Neuroprotective Agent for Cerebral Ischemic Stroke". . p. 2478 - 2490. Retrieved 2021/07/21.
• 2、 -. "Leonurine metabolite and preparation method thereof". Paragraph 0052; 0053; 0054. . Retrieved 2017/05/02.