(3R,4R,5S)-4-acetamido-5-guanidino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonic acid

Base Information

Chemical Name:(3R,4R,5S)-4-acetamido-5-guanidino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonic acid
CAS No.:949962-57-6
Molecular Formula:C₁₄H₂₇N₄O₅P
Molecular Weight:362.366
Hs Code.:

Synonyms:(3R,4R,5S)-4-acetamido-5-guanidino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonic acid

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Chemical Property of (3R,4R,5S)-4-acetamido-5-guanidino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonic acid

Chemical Property:

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Technology Process of (3R,4R,5S)-4-acetamido-5-guanidino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonic acid

There total 27 articles about (3R,4R,5S)-4-acetamido-5-guanidino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonic 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: 85.0%

: 1401808-94-3
C₁₈H₃₅N₄O₅P

: 949962-57-6
(3R,4R,5S)-4-acetamido-5-guanidino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonic acid

Guidance literature:: With trimethylsilyl bromide; In chloroform; at 25 ℃; for 24h;
DOI:10.1021/jm3008486

Reference yield:

: C₈H₁₅NO₄

: 949962-57-6
(3R,4R,5S)-4-acetamido-5-guanidino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonic acid

Guidance literature:: Multi-step reaction with 16 steps

1: pyridine / 3 h / 25 °C

2: hydrogenchloride / 1,4-dioxane; toluene; water / 24 h / 0 - 25 °C

3: toluene-4-sulfonic acid / toluene / 4 h / 80 °C

4: pyridine / dichloromethane / 2 h / -15 °C

5: sodium hydride; 15-crown-5 / N,N-dimethyl-formamide / 24 h / 25 °C

6: hydrogen; palladium on activated charcoal / ethanol / 24 h / 25 °C

7: sodium ethanolate / ethanol / 5 h / 25 °C

8: diphenyl phosphoryl azide; diisopropyl-carbodiimide; triphenylphosphine / tetrahydrofuran / 48 h / 25 °C

9: hydrogenchloride / ethanol / 1 h / Reflux

10: pyridine / dichloromethane / 2 h / -15 - -10 °C

11: potassium nitrite; 18-crown-6 ether / N,N-dimethyl-formamide / 24 h / 40 °C

12: trifluorormethanesulfonic acid / dichloromethane / 24 h / 25 °C

13: hydrogen / ethanol / 16 h / 25 °C

14: mercury dichloride; triethylamine / N,N-dimethyl-formamide / 0 - 25 °C

15: trifluoroacetic acid / dichloromethane / 1 h / 0 °C

16: trimethylsilyl bromide / chloroform / 24 h / 25 °C

With pyridine; hydrogenchloride; potassium nitrite; 15-crown-5; 18-crown-6 ether; trimethylsilyl bromide; trifluorormethanesulfonic acid; diphenyl phosphoryl azide; palladium on activated charcoal; hydrogen; sodium ethanolate; sodium hydride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; trifluoroacetic acid; mercury dichloride; diisopropyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm3008486

Reference yield:

: O-benzyl-3-acetamido-3-deoxy-α/β-D-ribofuranoside

: 949962-57-6
(3R,4R,5S)-4-acetamido-5-guanidino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonic acid

Guidance literature:: Multi-step reaction with 14 steps

1: toluene-4-sulfonic acid / toluene / 4 h / 80 °C

2: pyridine / dichloromethane / 2 h / -15 °C

3: sodium hydride; 15-crown-5 / N,N-dimethyl-formamide / 24 h / 25 °C

4: hydrogen; palladium on activated charcoal / ethanol / 24 h / 25 °C

5: sodium ethanolate / ethanol / 5 h / 25 °C

6: diphenyl phosphoryl azide; diisopropyl-carbodiimide; triphenylphosphine / tetrahydrofuran / 48 h / 25 °C

7: hydrogenchloride / ethanol / 1 h / Reflux

8: pyridine / dichloromethane / 2 h / -15 - -10 °C

9: potassium nitrite; 18-crown-6 ether / N,N-dimethyl-formamide / 24 h / 40 °C

10: trifluorormethanesulfonic acid / dichloromethane / 24 h / 25 °C

11: hydrogen / ethanol / 16 h / 25 °C

12: mercury dichloride; triethylamine / N,N-dimethyl-formamide / 0 - 25 °C

13: trifluoroacetic acid / dichloromethane / 1 h / 0 °C

14: trimethylsilyl bromide / chloroform / 24 h / 25 °C

With pyridine; hydrogenchloride; potassium nitrite; 15-crown-5; 18-crown-6 ether; trimethylsilyl bromide; trifluorormethanesulfonic acid; diphenyl phosphoryl azide; palladium on activated charcoal; hydrogen; sodium ethanolate; sodium hydride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; trifluoroacetic acid; mercury dichloride; diisopropyl-carbodiimide; In tetrahydrofuran; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm3008486