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

Base Information

Chemical Name:(3R,4R,5S)-4-Acetylamino-5-azido-3-methoxymethoxy-cyclohex-1-enecarboxylic acid methyl ester
CAS No.:187226-97-7
Molecular Formula:C₁₂H₁₈N₄O₅
Molecular Weight:298.299
Hs Code.:

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

Suppliers and Price of (3R,4R,5S)-4-Acetylamino-5-azido-3-methoxymethoxy-cyclohex-1-enecarboxylic acid methyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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

There total 11 articles about (3R,4R,5S)-4-Acetylamino-5-azido-3-methoxymethoxy-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: 76.0%

: 75-36-5
acetyl chloride

: 187226-93-3
(1R,5R,6R)-5-Methoxymethoxy-7-aza-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester

: 187226-97-7
(3R,4R,5S)-4-Acetylamino-5-azido-3-methoxymethoxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: (1R,5R,6R)-5-Methoxymethoxy-7-aza-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester; With sodium azide; ammonium chloride; In N,N-dimethyl-formamide; at 65 ℃; for 18h;

acetyl chloride; With pyridine; In dichloromethane;

Reference yield: 76.0%

: 75-36-5
acetyl chloride

: 187226-95-5
(3R,4R,5S)-4-Amino-5-azido-3-methoxymethoxy-cyclohex-1-enecarboxylic acid methyl ester

: 187226-97-7
(3R,4R,5S)-4-Acetylamino-5-azido-3-methoxymethoxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: In pyridine; dichloromethane;
DOI:10.1021/ja963036t

Reference yield:

: 113473-12-4
methyl (3R,4R,5R)-3,4-dihydroxy-5-<(p-tolylsulfonyl)oxy>-1-cyclohexene-1-carboxylate

: 187226-97-7
(3R,4R,5S)-4-Acetylamino-5-azido-3-methoxymethoxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / DBU / tetrahydrofuran / 12 h / Ambient temperature

2: 97 percent / diisopropylethylamine / CH₂Cl₂ / 3.5 h / Heating

3: 86 percent / NaN₃, NH₄Cl / methanol; H₂O / 15 h / Heating

4: 99 percent / triethylamine; CH₂Cl₂ / 0.75 h / 0 °C

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

6: 2.95 g / NaN₃, NH₄Cl / dimethylformamide / 21 h / 65 - 70 °C

7: 76 percent / CH₂Cl₂; pyridine

With sodium azide; ammonium 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