(3R,4R,5S)-4-Acetylamino-5-amino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid

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Chemical Name:(3R,4R,5S)-4-Acetylamino-5-amino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid
CAS No.:187226-99-9
Molecular Formula:C₁₁H₁₈N₂O₅
Molecular Weight:258.274
Hs Code.:

Synonyms:(3R,4R,5S)-4-Acetylamino-5-amino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid

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Chemical Property of (3R,4R,5S)-4-Acetylamino-5-amino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid

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Technology Process of (3R,4R,5S)-4-Acetylamino-5-amino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid

There total 12 articles about (3R,4R,5S)-4-Acetylamino-5-amino-3-methoxymethoxy-cyclohex-1-enecarboxylic 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: 92.0%

: 208720-84-7
(3R,4R,5S)-4-Acetylamino-5-amino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid methyl ester

: 187226-99-9
(3R,4R,5S)-4-Acetylamino-5-amino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid

Guidance literature:: With potassium hydroxide; In tetrahydrofuran; for 2.5h; under 760.051 Torr;

Reference yield:

: 113473-11-3
methyl 3 L-(3,4/5)-3,4,5-trihydroxy-3,4-O-isopropylidene-5-O-p-tolylsulfonyl-1-cyclohexene-1-carboxylate

: 187226-99-9
(3R,4R,5S)-4-Acetylamino-5-amino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 20.5 g / p-TsOH / methanol; CH₂Cl₂ / 4 h / Heating

2: 100 percent / DBU / tetrahydrofuran / 12 h / Ambient temperature

3: 97 percent / diisopropylethylamine / CH₂Cl₂ / 3.5 h / Heating

4: 86 percent / NaN₃, NH₄Cl / methanol; H₂O / 15 h / Heating

5: 99 percent / triethylamine; CH₂Cl₂ / 0.75 h / 0 °C

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

7: 2.95 g / NaN₃, NH₄Cl / dimethylformamide / 21 h / 65 - 70 °C

8: 76 percent / CH₂Cl₂; pyridine

9: H₂ / Lindlar catalyst / ethanol; H₂O / 760 Torr

10: 20 mg / KOH / tetrahydrofuran; H₂O / 1 h

With potassium hydroxide; sodium azide; hydrogen; ammonium chloride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; ethanol; 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

: 187226-99-9
(3R,4R,5S)-4-Acetylamino-5-amino-3-methoxymethoxy-cyclohex-1-enecarboxylic acid

Guidance literature:: Multi-step reaction with 8 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: 76 percent / CH₂Cl₂; pyridine

7: H₂ / Lindlar catalyst / ethanol; H₂O / 760 Torr

8: 20 mg / KOH / tetrahydrofuran; H₂O / 1 h

With potassium hydroxide; sodium azide; hydrogen; ammonium chloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; triethylamine; N,N-dimethyl-formamide;
DOI:10.1021/ja963036t