1,3,2’-triazido-5,6,3’-tri-O-benzyl paromamine

Base Information

• Chemical Name: 1,3,2’-triazido-5,6,3’-tri-O-benzyl paromamine
• CAS No.: 1624627-56-0
• Molecular Formula: C₃₃H₃₇N₉O₇
• Molecular Weight: 671.713
• Mol file: 1624627-56-0.mol

Synonyms:1,3,2’-triazido-5,6,3’-tri-O-benzyl paromamine

Chemical Property of 1,3,2’-triazido-5,6,3’-tri-O-benzyl paromamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3,2’-triazido-5,6,3’-tri-O-benzyl paromamine

There total 6 articles about 1,3,2’-triazido-5,6,3’-tri-O-benzyl paromamine 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: 77.0%

1,3,2’-triazido-5,6,3’-tri-O-benzyl-4’,6’-O-benzylidene paromamine (1624627-55-9) → 1,3,2’-triazido-5,6,3’-tri-O-benzyl paromamine (1624627-56-0)

Guidance literature:

With water; acetic acid; In tetrahydrofuran; at 60 ℃; Inert atmosphere;

DOI:10.1039/c4md00072b

Reference yield:

Paromamine (534-47-4,11030-86-7) → 1,3,2’-triazido-5,6,3’-tri-O-benzyl paromamine (1624627-56-0)

Guidance literature:

Multi-step reaction with 4 steps

1: triflic azide; copper(ll) sulfate pentahydrate; triethylamine / Inert atmosphere

2: camphorsulfonic acid / N,N-dimethyl-formamide / Inert atmosphere

3: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere

4: acetic acid / water / 60 °C / Inert atmosphere

With copper(ll) sulfate pentahydrate; triflic azide; sodium hydride; acetic acid; triethylamine; In water; N,N-dimethyl-formamide;

DOI:10.1002/cbic.201800549

Reference yield:

(2R,3S,4R,5R,6S)-5-azido-6-(((1R,2R,3S,4R,6S)-4, 6-diazido-2,3-dihydroxycyclohexyl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol (289505-10-8) → 1,3,2’-triazido-5,6,3’-tri-O-benzyl paromamine (1624627-56-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (1S)-10-camphorsulfonic acid / 1,2-dichloro-ethane / 2 h / Reflux; Inert atmosphere

2.1: sodium hydride / mineral oil; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

2.2: 0 - 26 °C

3.1: acetic acid; water / tetrahydrofuran / 60 °C / Inert atmosphere

With (1S)-10-camphorsulfonic acid; water; sodium hydride; acetic acid; In tetrahydrofuran; 1,2-dichloro-ethane; mineral oil;

DOI:10.1039/c4md00072b

upstream raw materials:

(2R,3S,4R,5R,6S)-5-azido-6-(((1R,2R,3S,4R,6S)-4, 6-diazido-2,3-dihydroxycyclohexyl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

1,3,2’-triazido-4’,6’-O-benzylideneparomamine

1,3,2’-triazido-5,6,3’-tri-O-benzyl-4’,6’-O-benzylidene paromamine

Paromamine

Downstream raw materials:

1,3,2’-triazido-5,6,3’-tri-O-benzyl-6’-O-(p-toluenesulfonyl)paromamine

1,3,2’,6’-tetraazido-5,6,3’-tri-O-benzylneamine

1,3,2’,6’-tetraazido-5,6,3’-tri-O-benzyl-4’-deoxy-4’-fluoro-4’-epineamine

1,3,2’,6’-tetraazido-5,6,3’-tri-O-benzyl-4’-deoxy-4’-fluoroneamine

Refernces

• 1、 Smolkin, Boris,Khononov, Alina,Pieńko, Tomasz,Shavit, Michal,Belakhov, Valery,Trylska, Joanna,Baasov, Timor. "Towards Catalytic Antibiotics: Redesign of Aminoglycosides To Catalytically Disable Bacterial Ribosomes". . p. 247 - 259. Retrieved 2019/01/04.