(3S,4R,5S)-4-Amino-5-azido-2-chloro-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid methyl ester

Base Information

Chemical Name:(3S,4R,5S)-4-Amino-5-azido-2-chloro-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid methyl ester
CAS No.:195244-46-3
Molecular Formula:C₁₃H₂₁ClN₄O₃
Molecular Weight:316.788
Hs Code.:

Synonyms:(3S,4R,5S)-4-Amino-5-azido-2-chloro-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid methyl ester

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Chemical Property of (3S,4R,5S)-4-Amino-5-azido-2-chloro-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid methyl ester

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Technology Process of (3S,4R,5S)-4-Amino-5-azido-2-chloro-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid methyl ester

There total 9 articles about (3S,4R,5S)-4-Amino-5-azido-2-chloro-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid methyl ester 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: 54.0%

: 195244-45-2
(1R,5S,6R)-4-Chloro-5-(1-ethyl-propoxy)-7-aza-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester

: 195244-46-3
(3S,4R,5S)-4-Amino-5-azido-2-chloro-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: With sodium azide; ammonium chloride; In N,N-dimethyl-formamide; at 70 ℃;
DOI:10.1016/S0960-894X(97)00331-4

Reference yield:

: 153919-36-9
methyl 3(S),4(S),5(R)-triacetoxy-2-chloro-1-cyclohexenecarboxylate

: 195244-46-3
(3S,4R,5S)-4-Amino-5-azido-2-chloro-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: CH₃ONa / methanol / Ambient temperature

2: p-TsOH / acetone / Heating

3: Et₃N / CH₂Cl₂ / Ambient temperature

4: HClO₄ / 40 °C

5: 1.) BH₃*Me₂S, TMSOTf, 2.) KHCO₃ / 1.) CH₂Cl₂, -20 to 0 deg C, 2.) MeOH, H₂O, 40 deg C

6: NaN₃, NH₄Cl / methanol; H₂O / Heating

7: Et₃N / CH₂Cl₂ / Ambient temperature

8: 1.) Ph₃P, 2.) Et₃N / 1.) THF, room temperature, 2.) H₂O, room temperature

9: 54 percent / NaN₃, NH₄Cl / dimethylformamide / 70 °C

With sodium azide; perchloric acid; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; sodium methylate; ammonium chloride; potassium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0960-894X(97)00331-4

Reference yield:

: 195244-38-3
(3S,4S,5R)-2-Chloro-3,4,5-trihydroxy-cyclohex-1-enecarboxylic acid methyl ester

: 195244-46-3
(3S,4R,5S)-4-Amino-5-azido-2-chloro-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: p-TsOH / acetone / Heating

2: Et₃N / CH₂Cl₂ / Ambient temperature

3: HClO₄ / 40 °C

4: 1.) BH₃*Me₂S, TMSOTf, 2.) KHCO₃ / 1.) CH₂Cl₂, -20 to 0 deg C, 2.) MeOH, H₂O, 40 deg C

5: NaN₃, NH₄Cl / methanol; H₂O / Heating

6: Et₃N / CH₂Cl₂ / Ambient temperature

7: 1.) Ph₃P, 2.) Et₃N / 1.) THF, room temperature, 2.) H₂O, room temperature

8: 54 percent / NaN₃, NH₄Cl / dimethylformamide / 70 °C

With sodium azide; perchloric acid; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; ammonium chloride; potassium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0960-894X(97)00331-4