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

Base Information

Chemical Name:(3R,4R,5S)-4-Acetylamino-5-azido-3-propoxy-cyclohex-1-enecarboxylic acid methyl ester
CAS No.:187226-68-2
Molecular Formula:C₁₃H₂₀N₄O₄
Molecular Weight:296.326
Hs Code.:

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

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

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

There total 25 articles about (3R,4R,5S)-4-Acetylamino-5-azido-3-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: 93.0%

: 75-36-5
acetyl chloride

: 208720-77-8
(3R,4R,5S)-4-Amino-5-azido-3-propoxy-cyclohex-1-enecarboxylic acid methyl ester

: 187226-68-2
(3R,4R,5S)-4-Acetylamino-5-azido-3-propoxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: With pyridine; In dichloromethane; at 0 ℃; for 1.5h;

Reference yield:

: 97373-88-1
methyl (1R,3R,4S,5R)-1,5-dihydroxy-3,4-(isopropylidenedioxy)cyclohexane-1-carboxylate

: 187226-68-2
(3R,4R,5S)-4-Acetylamino-5-azido-3-propoxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 92 percent / DMAP / pyridine / 72 h / Ambient temperature

2: 12 percent / SO₂Cl₂ / pyridine; CH₂Cl₂ / 5 h / -78 °C

3: 20.5 g / p-TsOH / methanol; CH₂Cl₂ / 4 h / Heating

4: 100 percent / DBU / tetrahydrofuran / 12 h / Ambient temperature

5: 97 percent / diisopropylethylamine / CH₂Cl₂ / 3.5 h / Heating

6: 86 percent / NaN₃, NH₄Cl / methanol; H₂O / 15 h / Heating

7: 99 percent / triethylamine; CH₂Cl₂ / 0.75 h / 0 °C

8: 1.) PPh₃, 2.) Et₃N / 1.) THF, rt, 3 h, rt, 2.) H₂O, THF, rt, 12 h

9: 2.95 g / NaN₃, NH₄Cl / dimethylformamide / 21 h / 65 - 70 °C

10: 99 percent / HCl / methanol / 4 h / Ambient temperature

11: 1.) Et₃N, 2.) MeSO₂Cl, Et₃N / 1.) CH₂Cl₂, 0 deg C, 1 h; rt, 2 h, 2.) CH₂Cl₂, 0 deg C, 1 h; rt 22 h

12: BF₃*Et₂O / 2 h / 70 - 75 °C

13: DMAP / pyridine / Ambient temperature

With hydrogenchloride; dmap; sodium azide; sulfuryl dichloride; boron trifluoride diethyl etherate; ammonium chloride; toluene-4-sulfonic acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; triethylamine; N,N-dimethyl-formamide;
DOI:10.1021/ja963036t

Reference yield:

: 76985-84-7
(-)-methyl (1β,2α,6β)-2-hydroxy-7-oxabicyclo<4,1,0>hept-3-ene-4-carboxylate

: 187226-68-2
(3R,4R,5S)-4-Acetylamino-5-azido-3-propoxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 97 percent / diisopropylethylamine / CH₂Cl₂ / 3.5 h / Heating

2: 86 percent / NaN₃, NH₄Cl / methanol; H₂O / 15 h / Heating

3: 99 percent / triethylamine; CH₂Cl₂ / 0.75 h / 0 °C

4: 1.) PPh₃, 2.) Et₃N / 1.) THF, rt, 3 h, rt, 2.) H₂O, THF, rt, 12 h

5: 2.95 g / NaN₃, NH₄Cl / dimethylformamide / 21 h / 65 - 70 °C

6: 99 percent / HCl / methanol / 4 h / Ambient temperature

7: 1.) Et₃N, 2.) MeSO₂Cl, Et₃N / 1.) CH₂Cl₂, 0 deg C, 1 h; rt, 2 h, 2.) CH₂Cl₂, 0 deg C, 1 h; rt 22 h

8: BF₃*Et₂O / 2 h / 70 - 75 °C

9: DMAP / pyridine / Ambient temperature

With hydrogenchloride; dmap; sodium azide; boron trifluoride diethyl etherate; ammonium chloride; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In pyridine; methanol; dichloromethane; water; triethylamine; N,N-dimethyl-formamide;
DOI:10.1021/ja963036t