1,3,2′,6′,2?,6?-hexa-N-(tert-butoxycarbonyl)-5″-O-(2,4,6-triisopropylbenzenesulfonyl)-neomycin

Base Information

• Chemical Name: 1,3,2′,6′,2?,6?-hexa-N-(tert-butoxycarbonyl)-5″-O-(2,4,6-triisopropylbenzenesulfonyl)-neomycin
• CAS No.: 241820-93-9
• Molecular Formula: C₆₈H₁₁₆N₆O₂₇S
• Molecular Weight: 1481.76
• Mol file: 241820-93-9.mol

Synonyms:1,3,2′,6′,2?,6?-hexa-N-(tert-butoxycarbonyl)-5″-O-(2,4,6-triisopropylbenzenesulfonyl)-neomycin

Chemical Property of 1,3,2′,6′,2?,6?-hexa-N-(tert-butoxycarbonyl)-5″-O-(2,4,6-triisopropylbenzenesulfonyl)-neomycin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3,2′,6′,2?,6?-hexa-N-(tert-butoxycarbonyl)-5″-O-(2,4,6-triisopropylbenzenesulfonyl)-neomycin

There total 2 articles about 1,3,2′,6′,2?,6?-hexa-N-(tert-butoxycarbonyl)-5″-O-(2,4,6-triisopropylbenzenesulfonyl)-neomycin 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: 75.0%

2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) + hexa-N-Boc neomycin B (241820-92-8) → 1,3,2′,6′,2?,6?-hexa-N-(tert-butoxycarbonyl)-5″-O-(2,4,6-triisopropylbenzenesulfonyl)-neomycin (241820-93-9)

Guidance literature:

With pyridine; at 20 ℃; for 20h;

DOI:10.1021/ja993387i

Reference yield:

neomycin B (119-04-0) + 2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) + di-tert-butyl dicarbonate (24424-99-5) → 1,3,2′,6′,2?,6?-hexa-N-(tert-butoxycarbonyl)-5″-O-(2,4,6-triisopropylbenzenesulfonyl)-neomycin (241820-93-9)

Guidance literature:

neomycin B; di-tert-butyl dicarbonate; With sodium carbonate; In methanol; water; at 20 ℃; for 18h;

2,4,6-triisopropylphenylsulfonyl chloride; With pyridine; at 20 ℃; for 40h;

DOI:10.1039/c7ra07178g

Reference yield: 100.0%

1,3,2′,6′,2?,6?-hexa-N-(tert-butoxycarbonyl)-5″-O-(2,4,6-triisopropylbenzenesulfonyl)-neomycin (241820-93-9) → 5″-azide-1,3,2′,6′,2′″,6′″-hexa-N-(tert-butoxycarbonyl)-5″-deoxy-neomycin B (849676-07-9)

Guidance literature:

With sodium azide; In water; N,N-dimethyl-formamide; at 90 ℃; Temperature; Time;

upstream raw materials:

2,4,6-triisopropylphenylsulfonyl chloride

hexa-N-Boc neomycin B

neomycin B

di-tert-butyl dicarbonate

Downstream raw materials:

C₅₇H₁₀₂N₆O₂₅S₂

C₅₅H₉₉N₇O₂₄S

5″-azide-1,3,2′,6′,2′″,6′″-hexa-N-(tert-butoxycarbonyl)-5″-deoxy-neomycin B

Refernces

• 1、 Wang, Siwen,Singh, Mandeep,Ling, Mingheng,Li, Danni,Christison, Krege M.,Lin-Cereghino, Joan,Lin-Cereghino, Geoff P.,Xue, Liang. "Synthesis of nucleobase-neomycin conjugates and evaluation of their DNA binding, cytotoxicities, and antibacterial properties". . p. 1517 - 1527. Retrieved 2018/04/02.
• 2、 Yan, Hao,Bhattarai, Umesh,Guo, Zhi-Fo,Liang, Fu-Sen. "Regulating miRNA-21 Biogenesis by Bifunctional Small Molecules". supporting information. p. 4987 - 4990. Retrieved 2017/05/04.