(3R,4S,5S)-4-Acetylamino-5-azido-3-butyl-cyclohex-1-enecarboxylic acid methyl ester

Base Information

Chemical Name:(3R,4S,5S)-4-Acetylamino-5-azido-3-butyl-cyclohex-1-enecarboxylic acid methyl ester
CAS No.:221387-14-0
Molecular Formula:C₁₄H₂₂N₄O₃
Molecular Weight:294.354
Hs Code.:

Synonyms:(3R,4S,5S)-4-Acetylamino-5-azido-3-butyl-cyclohex-1-enecarboxylic acid methyl ester

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Chemical Property of (3R,4S,5S)-4-Acetylamino-5-azido-3-butyl-cyclohex-1-enecarboxylic acid methyl ester

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Technology Process of (3R,4S,5S)-4-Acetylamino-5-azido-3-butyl-cyclohex-1-enecarboxylic acid methyl ester

There total 9 articles about (3R,4S,5S)-4-Acetylamino-5-azido-3-butyl-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: 68.0%

: 75-36-5
acetyl chloride

: 221387-12-8
(3R,4S,5S)-4-Amino-5-azido-3-butyl-cyclohex-1-enecarboxylic acid methyl ester

: 221387-14-0
(3R,4S,5S)-4-Acetylamino-5-azido-3-butyl-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: With pyridine;
DOI:10.1016/S0960-894X(97)00332-6

Reference yield:

: 221386-99-8
(4aR,6S,8aR)-8-But-(E)-ylidene-2,3-dimethoxy-2,3-dimethyl-6-triethylsilanyloxy-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

: 221387-14-0
(3R,4S,5S)-4-Acetylamino-5-azido-3-butyl-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 97 percent / H₂ / Pd/C

2: 77 percent / TBAF / tetrahydrofuran

3: 1.) SO₂Cl₂, 2.) MeOH

4: 75 percent / TFA / CH₂Cl₂

5: 1.) MsCl, Et₃N, 2.) DBU / 2.) THF

6: 1.) NaN₃, NH₄Cl, 2.) MsCl, Et₃N, 3.) PPh₃, 4.) Et₃N

7: 86 percent / NaN₃, NH₄Cl / dimethylformamide

8: 68 percent / pyridine

With pyridine; methanol; sodium azide; sulfuryl dichloride; tetrabutyl ammonium fluoride; hydrogen; ammonium chloride; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(97)00332-6

Reference yield:

: 221386-97-6
(4aR,6R,8aS)-6-Hydroxy-2,3-dimethoxy-2,3-dimethyl-8-oxo-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

: 221387-14-0
(3R,4S,5S)-4-Acetylamino-5-azido-3-butyl-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 81 percent / n-BuLi / tetrahydrofuran

2: 93 percent / 2,6-lutidine

3: 97 percent / H₂ / Pd/C

4: 77 percent / TBAF / tetrahydrofuran

5: 1.) SO₂Cl₂, 2.) MeOH

6: 75 percent / TFA / CH₂Cl₂

7: 1.) MsCl, Et₃N, 2.) DBU / 2.) THF

8: 1.) NaN₃, NH₄Cl, 2.) MsCl, Et₃N, 3.) PPh₃, 4.) Et₃N

9: 86 percent / NaN₃, NH₄Cl / dimethylformamide

10: 68 percent / pyridine

With pyridine; 2,6-dimethylpyridine; methanol; n-butyllithium; sodium azide; sulfuryl dichloride; tetrabutyl ammonium fluoride; hydrogen; ammonium chloride; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(97)00332-6