(E)-(R)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-(toluene-4-sulfonyl)-1-oxa-4-aza-cyclotetradec-7-ene-10,10-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: (E)-(R)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-(toluene-4-sulfonyl)-1-oxa-4-aza-cyclotetradec-7-ene-10,10-dicarboxylic acid dimethyl ester
• CAS No.: 295337-56-3
• Molecular Formula: C₃₇H₅₁NO₁₀S
• Molecular Weight: 701.879
• Mol file: 295337-56-3.mol

Synonyms:(E)-(R)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-(toluene-4-sulfonyl)-1-oxa-4-aza-cyclotetradec-7-ene-10,10-dicarboxylic acid dimethyl ester

Chemical Property of (E)-(R)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-(toluene-4-sulfonyl)-1-oxa-4-aza-cyclotetradec-7-ene-10,10-dicarboxylic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(R)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-(toluene-4-sulfonyl)-1-oxa-4-aza-cyclotetradec-7-ene-10,10-dicarboxylic acid dimethyl ester

There total 11 articles about (E)-(R)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-(toluene-4-sulfonyl)-1-oxa-4-aza-cyclotetradec-7-ene-10,10-dicarboxylic acid dimethyl 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: 75.0%

2-(4-{(R)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-[((E)-5-chloro-pent-3-enyl)-(toluene-4-sulfonyl)-amino]-propoxy}-butyl)-malonic acid dimethyl ester (295337-54-1) → (E)-(R)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-(toluene-4-sulfonyl)-1-oxa-4-aza-cyclotetradec-7-ene-10,10-dicarboxylic acid dimethyl ester (295337-56-3)

Guidance literature:

With caesium carbonate; In acetonitrile; at 70 ℃; for 40h;

DOI:10.1016/S0040-4039(00)00710-3

Reference yield:

2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran (194861-23-9) → (E)-(R)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-(toluene-4-sulfonyl)-1-oxa-4-aza-cyclotetradec-7-ene-10,10-dicarboxylic acid dimethyl ester (295337-56-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: pyridinium p-toluenesulfonate / 1,2-dichloro-ethane / 16 h / 75 °C

2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 3 h / 20 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C

4.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / dichloromethane / 4 h / 20 °C

4.2: DDQ / 22; 15 / 4 h / 20 °C

5.1: 1H-imidazole; iodine; triphenylphosphine / toluene; acetonitrile / 10 h / 20 °C

6.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 12 h / 20 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C

8.1: 1H-imidazole; N-chloro-succinimide; triphenylphosphine / tetrahydrofuran / 8 h / 20 °C

9.1: caesium carbonate / acetonitrile / 40 h / 70 °C

With 1H-imidazole; N-chloro-succinimide; lithium aluminium tetrahydride; 2,6-di-tert-butyl-pyridine; tetrabutyl ammonium fluoride; iodine; silver trifluoromethanesulfonate; pyridinium p-toluenesulfonate; sodium hydride; caesium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Etherification / 2.1: Mitsunobu reaction / 3.1: Reduction / 4.1: Condensation / 4.2: deprotection / 5.1: Iodination / 6.1: Substitution / 7.1: Hydrolysis / 8.1: Chlorination / 9.1: Cyclization;

DOI:10.1016/S0040-4039(00)00710-3

Reference yield:

(S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonylamino)-propionic acid methyl ester (294844-18-1) → (E)-(R)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-(toluene-4-sulfonyl)-1-oxa-4-aza-cyclotetradec-7-ene-10,10-dicarboxylic acid dimethyl ester (295337-56-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 3 h / 20 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C

3.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / dichloromethane / 4 h / 20 °C

3.2: DDQ / 22; 15 / 4 h / 20 °C

4.1: 1H-imidazole; iodine; triphenylphosphine / toluene; acetonitrile / 10 h / 20 °C

5.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 12 h / 20 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C

7.1: 1H-imidazole; N-chloro-succinimide; triphenylphosphine / tetrahydrofuran / 8 h / 20 °C

8.1: caesium carbonate / acetonitrile / 40 h / 70 °C

With 1H-imidazole; N-chloro-succinimide; lithium aluminium tetrahydride; 2,6-di-tert-butyl-pyridine; tetrabutyl ammonium fluoride; iodine; silver trifluoromethanesulfonate; sodium hydride; caesium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Mitsunobu reaction / 2.1: Reduction / 3.1: Condensation / 3.2: deprotection / 4.1: Iodination / 5.1: Substitution / 6.1: Hydrolysis / 7.1: Chlorination / 8.1: Cyclization;

DOI:10.1016/S0040-4039(00)00710-3

upstream raw materials:

2-(4-{(R)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-[((E)-5-chloro-pent-3-enyl)-(toluene-4-sulfonyl)-amino]-propoxy}-butyl)-malonic acid dimethyl ester

2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran

(S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonylamino)-propionic acid methyl ester

2-(4-{(R)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-[((E)-5-hydroxy-pent-3-enyl)-(toluene-4-sulfonyl)-amino]-propoxy}-butyl)-malonic acid dimethyl ester