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

Base Information

• Chemical Name: 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
• CAS No.: 66065-90-5
• Molecular Formula: C₂₅H₃₈F₆N₄O₁₀*H₂O₄S
• Molecular Weight: 766.667

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 1 articles about 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 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: 86.0%

3,2'-bis-N-trifluoroacetylgentamicin C1 (54619-80-6) → 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)

Guidance literature:

With sulfuric acid; 3,5-di-tert-butyl-o-benzoquinone; In methanol; at 25 ℃; for 28h; pH = 2.5 - 3.0;

DOI:10.1039/P19810002168

Reference yield: 17.0%

ethanolamine (141-43-5) + 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) → 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-(2-hydroxyethyl)gentamicin C1 (67591-13-3,67650-41-3) + 1-epi-N-(2-hydroxyethyl)gentamicin C1 (67591-13-3,67650-41-3)

Guidance literature:

With hydrogenchloride; ammonium hydroxide; sodium cyanoborohydride; Yield given. Multistep reaction; 1.) pH = 5.5 - 6, 25 deg C, 17 h, 2.) 25 deg C, 48 h;

DOI:10.1039/P19810002168

Reference yield: 16.0%

phenethylamine (64-04-0) + 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) → 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-(2-phenylethyl)gentamicin C1 (67591-14-4,67650-42-4) + 1-epi-N-(2-phenylethyl)gentamicin C1 (67591-14-4,67650-42-4)

Guidance literature:

With hydrogenchloride; ammonium hydroxide; sodium cyanoborohydride; Yield given. Multistep reaction; 1.) methanol, pH = 5.5 - 6, 25 deg C, 19 h, 2.) 25 deg C, 116 h;

DOI:10.1039/P19810002168

upstream raw materials:

3,2'-bis-N-trifluoroacetylgentamicin C₁

Downstream raw materials:

1-deamino-1-hydroxygentamicin C₁

1-deamino-1-epi-hydroxygentamicin C₁

1-N-(2-hydroxyethyl)gentamicin C₁

1-epi-N-(2-hydroxyethyl)gentamicin C₁

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