1-epi-N-isopropylentamicin C₁

Base Information

• Chemical Name: 1-epi-N-isopropylentamicin C₁
• CAS No.: 67591-12-2
• Molecular Formula: C₂₄H₄₉N₅O₇
• Molecular Weight: 519.682

Synonyms:

Chemical Property of 1-epi-N-isopropylentamicin C₁

Chemical Property:

Purity/Quality:

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Technology Process of 1-epi-N-isopropylentamicin C₁

There total 4 articles about 1-epi-N-isopropylentamicin C₁ 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: 3.0%

N-{(1S,2R,3S,4R)-4-((2R,3R,4R,5R)-3,5-Dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-3-hydroxy-2-[(2R,3R,6S)-6-(1-methylamino-ethyl)-3-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-yloxy]-5-oxo-cyclohexyl}-2,2,2-trifluoro-acetamide; compound with sulfuric acid (66065-90-5) + isopropylamine (75-31-0) → 1-deamino-1-hydroxygentamicin C1 (66065-94-9,66101-44-8) + 1-deamino-1-epi-hydroxygentamicin C1 (66065-94-9,66101-44-8) + 1-N-isopropylentamicin C1 (67591-12-2,67672-79-1) + 1-epi-N-isopropylentamicin C1 (67591-12-2,67672-79-1)

Guidance literature:

With hydrogenchloride; methanol; ammonium hydroxide; sodium cyanoborohydride; Yield given. Multistep reaction; 1.) pH = 5.5 - 6, 25 deg C, 16 h, 2.) 25 deg C, 72 h;

DOI:10.1039/P19810002168

Reference yield: 3.0%

N-{(1S,2R,3S,4R)-4-((2R,3R,4R,5R)-3,5-Dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-3-hydroxy-2-[(2R,3R,6S)-6-(1-methylamino-ethyl)-3-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-yloxy]-5-oxo-cyclohexyl}-2,2,2-trifluoro-acetamide; compound with sulfuric acid (66065-90-5) + isopropylamine (75-31-0) → 1-deamino-1-hydroxygentamicin C1 (66065-94-9,66101-44-8) + 1-deamino-1-epi-hydroxygentamicin C1 (66065-94-9,66101-44-8) + 1-N-isopropylentamicin C1 (67591-12-2,67672-79-1) + 1-epi-N-isopropylentamicin C1 (67591-12-2,67672-79-1)

Guidance literature:

With hydrogenchloride; methanol; ammonium hydroxide; sodium cyanoborohydride; Yield given. Multistep reaction; 1.) pH = 5.5 - 6, 25 deg C, 16 h, 2.) 25 deg C, 72 h;

DOI:10.1039/P19810002168

Reference yield:

3,2'-bis-N-trifluoroacetylgentamicin C1 (54619-80-6) → 1-N-isopropylentamicin C1 (67591-12-2,67672-79-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / 3,5-di-t-butyl-1,2-benzoquinone, 1M-sulphuric acid / methanol / 28 h / 25 °C / pH = 2.5 - 3.0

2: 3 percent / 1.) methanol, hydrogen chloride, sodium cyanoborohydride, 2.) conc. ammonium hydroxide / 1.) pH = 5.5 - 6, 25 deg C, 16 h, 2.) 25 deg C, 72 h

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

DOI:10.1039/P19810002168

upstream raw materials:

N-{(1S,2R,3S,4R)-4-((2R,3R,4R,5R)-3,5-Dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-3-hydroxy-2-[(2R,3R,6S)-6-(1-methylamino-ethyl)-3-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-yloxy]-5-oxo-cyclohexyl}-2,2,2-trifluoro-acetamide; compound with sulfuric acid

isopropylamine

3,2'-bis-N-trifluoroacetylgentamicin C₁

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