ethyl (3R,4R,5S)-4-acetamido-5-(1-(benzyloxycarbonyl)-2-ethylguanidino)-3-(pentan-3-yloxy)-cyclohex-1-enecarboxylate

Base Information

Chemical Name:ethyl (3R,4R,5S)-4-acetamido-5-(1-(benzyloxycarbonyl)-2-ethylguanidino)-3-(pentan-3-yloxy)-cyclohex-1-enecarboxylate
CAS No.:1588477-10-4
Molecular Formula:C₂₇H₄₀N₄O₆
Molecular Weight:516.638
Hs Code.:

Synonyms:ethyl (3R,4R,5S)-4-acetamido-5-(1-(benzyloxycarbonyl)-2-ethylguanidino)-3-(pentan-3-yloxy)-cyclohex-1-enecarboxylate

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Chemical Property of ethyl (3R,4R,5S)-4-acetamido-5-(1-(benzyloxycarbonyl)-2-ethylguanidino)-3-(pentan-3-yloxy)-cyclohex-1-enecarboxylate

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Technology Process of ethyl (3R,4R,5S)-4-acetamido-5-(1-(benzyloxycarbonyl)-2-ethylguanidino)-3-(pentan-3-yloxy)-cyclohex-1-enecarboxylate

There total 9 articles about ethyl (3R,4R,5S)-4-acetamido-5-(1-(benzyloxycarbonyl)-2-ethylguanidino)-3-(pentan-3-yloxy)-cyclohex-1-enecarboxylate 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: 93.0%

: 1588477-08-0
(3R,4R,5S)-ethyl 4-acetamido-5-(3-((benzyloxy)carbonyl)thioureido)-3-(pentan-3-yloxy)-cyclohex-1-enecarboxylate

: 75-04-7,85404-22-4
ethylamine

: 1588477-10-4
ethyl (3R,4R,5S)-4-acetamido-5-(1-(benzyloxycarbonyl)-2-ethylguanidino)-3-(pentan-3-yloxy)-cyclohex-1-enecarboxylate

Guidance literature:: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20 ℃;
DOI:10.1021/jm401977j

Reference yield:

: 101769-63-5
(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester

: 1588477-10-4
ethyl (3R,4R,5S)-4-acetamido-5-(1-(benzyloxycarbonyl)-2-ethylguanidino)-3-(pentan-3-yloxy)-cyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: dmap; triethylamine / ethyl acetate / 1.5 h / 0 °C

2.1: sodium azide / acetone; water / 4 h / 0 °C

3.1: toluene / 5.5 h / 120 °C / Reflux

3.2: 16 h / 20 °C / Cooling with ice

4.1: sulfuric acid / ethanol / 16 h / 70 °C

4.2: 4.5 h / 20 °C

5.1: sodium azide / water; ethanol / 8 h / Reflux

6.1: 5% Pd-CaCO3; hydrogen / ethanol / 16 h / 20 °C

7.1: triethylamine / dichloromethane / 1.5 h / 20 °C

8.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

With dmap; sodium azide; sulfuric acid; 5% Pd-CaCO3; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In ethanol; dichloromethane; water; ethyl acetate; acetone; toluene;
DOI:10.1021/jm401977j

Reference yield:

: 138-59-0
shikimic acid

: 1588477-10-4
ethyl (3R,4R,5S)-4-acetamido-5-(1-(benzyloxycarbonyl)-2-ethylguanidino)-3-(pentan-3-yloxy)-cyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: thionyl chloride / 2.5 h / 85 °C

2.1: dmap; triethylamine / ethyl acetate / 1.5 h / 0 °C

3.1: sodium azide / acetone; water / 4 h / 0 °C

4.1: toluene / 5.5 h / 120 °C / Reflux

4.2: 16 h / 20 °C / Cooling with ice

5.1: sulfuric acid / ethanol / 16 h / 70 °C

5.2: 4.5 h / 20 °C

6.1: sodium azide / water; ethanol / 8 h / Reflux

7.1: 5% Pd-CaCO3; hydrogen / ethanol / 16 h / 20 °C

8.1: triethylamine / dichloromethane / 1.5 h / 20 °C

9.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

With dmap; thionyl chloride; sodium azide; sulfuric acid; 5% Pd-CaCO3; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In ethanol; dichloromethane; water; ethyl acetate; acetone; toluene;
DOI:10.1021/jm401977j