3,2',6'-tri-N-acetylsisomicin

Base Information

• Chemical Name: 3,2',6'-tri-N-acetylsisomicin
• CAS No.: 66065-86-9
• Molecular Formula: C₂₅H₄₃N₅O₁₀
• Molecular Weight: 573.644
• Mol file: 66065-86-9.mol

Synonyms:3,2',6'-tri-N-acetylsisomicin

Chemical Property of 3,2',6'-tri-N-acetylsisomicin

Chemical Property:

• Boiling Point: 931.7±65.0 °C(Predicted)
• Density: 1.36±0.1 g/cm3(Predicted)

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3,2',6'-tri-N-acetylsisomicin

There total 3 articles about 3,2',6'-tri-N-acetylsisomicin 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: 96.0%

sisomicin (32385-11-8) + acetic anhydride (108-24-7) → 3,2',6'-tri-N-acetylsisomicin (66065-86-9)

Guidance literature:

sisomicin; With zinc(II) acetate dihydrate; In methanol; at 20 ℃; for 15h;

acetic anhydride; With triethylamine; In tetrahydrofuran; at 20 ℃; for 1h; Time;

DOI:10.1021/op000076f

Reference yield:

3,2',6'-tri-N-acetyl-1-deamino-1-oxosisomicin (66065-91-6) → N-[(1S,2R,3R,4S)-2-[(2S,3R)-3-Acetylamino-6-(acetylamino-methyl)-3,4-dihydro-2H-pyran-2-yloxy]-5-amino-4-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-3-hydroxy-cyclohexyl]-acetamide (66065-86-9,67777-22-4)

Guidance literature:

With ammonium acetate; hydrogenchloride; sodium cyanoborohydride; In methanol; 1.) pH = 5, 25 deg C, 7 h, 2.) 25 deg C, 18 h;

DOI:10.1039/P19810002168

Reference yield:

3,2',6'-tri-N-acetylsisomicin (66065-86-9) → N-[(1S,2R,3R,4S)-2-[(2S,3R)-3-Acetylamino-6-(acetylamino-methyl)-3,4-dihydro-2H-pyran-2-yloxy]-5-amino-4-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-3-hydroxy-cyclohexyl]-acetamide (66065-86-9,67777-22-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / 3,5-di-t-butyl-1,2-benzoquinone, 1M-sulphuric acid / methanol / 40 h / 25 °C / pH = 3

2: ammonium acetate, hydrogen chloride, sodium cyanoborohydride / methanol / 1.) pH = 5, 25 deg C, 7 h, 2.) 25 deg C, 18 h

With ammonium acetate; hydrogenchloride; sulfuric acid; 3,5-di-tert-butyl-o-benzoquinone; sodium cyanoborohydride; In methanol;

DOI:10.1039/P19810002168

upstream raw materials:

3,2',6'-tri-N-acetyl-1-deamino-1-oxosisomicin

sisomicin

acetic anhydride

Downstream raw materials:

1-deamino-2-deoxy-1-epi-hydroxystreptamine

sisomicin

1-N-carboxamidosisomicin

1-N-(methylcarboxamido)sisomicin

Refernces

• 1、 Nagabhushan, Tattanahalli L.,Turner, William N.,Tsai, Hsinghan,Jaret, Robert S.,Schumacher, Doris,et al.. "THE SYNTHESIS OF NETILMICIN via COMPLEXING OF VICINAL AND NON-VICINAL AMINO-HYDROXYL GROUP PAIRS WITH DIVALENT TRANSITION-METAL CATIONS". . p. 243 - 250. Retrieved 2007/10/02.