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

Base Information

• Chemical Name: (3R,4R,5S)-5-Azido-4-methanesulfonylamino-3-propoxy-cyclohex-1-enecarboxylic acid methyl ester
• CAS No.: 208720-60-9
• Molecular Formula: C₁₂H₂₀N₄O₅S
• Molecular Weight: 332.381
• Mol file: 208720-60-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about (3R,4R,5S)-5-Azido-4-methanesulfonylamino-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: 79.0%

methanesulfonyl chloride (124-63-0) + (3R,4R,5S)-4-Amino-5-azido-3-propoxy-cyclohex-1-enecarboxylic acid methyl ester (208720-77-8) → (3R,4R,5S)-5-Azido-4-methanesulfonylamino-3-propoxy-cyclohex-1-enecarboxylic acid methyl ester (208720-60-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 1.5h;

Reference yield:

(3aR,5S,7R,7aR)-5-Hydroxy-2,2-dimethyl-7-(toluene-4-sulfonyloxy)-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester (187227-25-4) → (3R,4R,5S)-5-Azido-4-methanesulfonylamino-3-propoxy-cyclohex-1-enecarboxylic acid methyl ester (208720-60-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: pyridine; methanol; sulfuryl dichloride / dichloromethane / 17 h / -78 - 20 °C

1.2: 4 h / Reflux

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 12 h / 0 - 20 °C

3.1: benzene / ethanol / 2 h

3.2: 16 h / Darkness

4.1: sodium azide; ammonium chloride / methanol; water / 18 h / Reflux

5.1: dmap; triethylamine / dichloromethane / 2 h / 0 °C

6.1: triphenylphosphine / tetrahydrofuran / 3 h / 20 °C

7.1: hydrogen / ethanol / 0.83 h / 20 °C / 760.05 Torr

8.1: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 16 h / 70 °C

9.1: dmap; triethylamine / dichloromethane / 1.5 h / 0 - 20 °C

With pyridine; methanol; dmap; sodium azide; sulfuryl dichloride; hydrogen; ammonium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; benzene; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

C12H17N3O6S → (3R,4R,5S)-5-Azido-4-methanesulfonylamino-3-propoxy-cyclohex-1-enecarboxylic acid methyl ester (208720-60-9)

Guidance literature:

Multi-step reaction with 4 steps

1: triphenylphosphine / tetrahydrofuran / 3 h / 20 °C

2: hydrogen / ethanol / 0.83 h / 20 °C / 760.05 Torr

3: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 16 h / 70 °C

4: dmap; triethylamine / dichloromethane / 1.5 h / 0 - 20 °C

With dmap; sodium azide; hydrogen; ammonium chloride; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

methanesulfonyl chloride

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

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

(3aR,5S,7R,7aR)-5-Hydroxy-2,2-dimethyl-7-(toluene-4-sulfonyloxy)-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester