(3R,4R,5S)-4-acetamido-5-(N²,N³-bis(tert-butoxycarbonyl)guanidino)-3-propoxy-1-cyclohexene-1-carboxylic acid

Base Information

• Chemical Name: (3R,4R,5S)-4-acetamido-5-(N²,N³-bis(tert-butoxycarbonyl)guanidino)-3-propoxy-1-cyclohexene-1-carboxylic acid
• CAS No.: 208589-19-9
• Molecular Formula: C₂₄H₄₀N₄O₈
• Molecular Weight: 512.604

Synonyms:(3R,4R,5S)-4-acetamido-5-(N²,N³-bis(tert-butoxycarbonyl)guanidino)-3-propoxy-1-cyclohexene-1-carboxylic acid

Chemical Property of (3R,4R,5S)-4-acetamido-5-(N²,N³-bis(tert-butoxycarbonyl)guanidino)-3-propoxy-1-cyclohexene-1-carboxylic acid

Chemical Property:

Purity/Quality:

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Technology Process of (3R,4R,5S)-4-acetamido-5-(N²,N³-bis(tert-butoxycarbonyl)guanidino)-3-propoxy-1-cyclohexene-1-carboxylic acid

There total 15 articles about (3R,4R,5S)-4-acetamido-5-(N²,N³-bis(tert-butoxycarbonyl)guanidino)-3-propoxy-1-cyclohexene-1-carboxylic 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: 90.0%

tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate (145013-05-4) + (3R,4R,5S)-4-Acetylamino-5-amino-3-propoxy-cyclohex-1-enecarboxylic acid methyl ester (208589-18-8) → (3R,4R,5S)-4-acetamido-5-(N2,N3-bis(tert-butoxycarbonyl)guanidino)-3-propoxy-1-cyclohexene-1-carboxylic acid (208589-19-9)

Guidance literature:

With triethylamine; mercury dichloride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 1h;

DOI:10.1021/jm980162u

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)-4-acetamido-5-(N2,N3-bis(tert-butoxycarbonyl)guanidino)-3-propoxy-1-cyclohexene-1-carboxylic acid (208589-19-9)

Guidance literature:

Multi-step reaction with 11 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: pyridine / dichloromethane / 1.5 h / 0 °C

10.1: triphenylphosphine / water; tetrahydrofuran / 42.5 h / 20 °C

11.1: N,N-dimethyl-formamide / 1 h / 0 °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:

(3R,4R,5S)-4-Amino-5-azido-3-propoxy-cyclohex-1-enecarboxylic acid methyl ester (208720-77-8) → (3R,4R,5S)-4-acetamido-5-(N2,N3-bis(tert-butoxycarbonyl)guanidino)-3-propoxy-1-cyclohexene-1-carboxylic acid (208589-19-9)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / dichloromethane / 1.5 h / 0 °C

2: triphenylphosphine / water; tetrahydrofuran / 42.5 h / 20 °C

3: N,N-dimethyl-formamide / 1 h / 0 °C

With pyridine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate

(3R,4R,5S)-4-Acetylamino-5-amino-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

Downstream raw materials:

C₂₃H₃₈N₄O₈

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