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

Base Information

• Chemical Name: 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
• CAS No.: 295337-53-0
• Molecular Formula: C₃₇H₅₃NO₁₁S
• Molecular Weight: 719.894
• Mol file: 295337-53-0.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 9 articles about 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 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: 91.0%

2-(4-{(R)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-[[(E)-5-(tert-butyl-diphenyl-silanyloxy)-pent-3-enyl]-(toluene-4-sulfonyl)-amino]-propoxy}-butyl)-malonic acid dimethyl ester (295337-51-8) → 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 (295337-53-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 5h;

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

Reference yield:

2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran (194861-23-9) → 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 (295337-53-0)

Guidance literature:

Multi-step reaction with 7 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

With 1H-imidazole; lithium aluminium tetrahydride; 2,6-di-tert-butyl-pyridine; tetrabutyl ammonium fluoride; iodine; silver trifluoromethanesulfonate; pyridinium p-toluenesulfonate; sodium hydride; 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;

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) → 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 (295337-53-0)

Guidance literature:

Multi-step reaction with 6 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

With 1H-imidazole; lithium aluminium tetrahydride; 2,6-di-tert-butyl-pyridine; tetrabutyl ammonium fluoride; iodine; silver trifluoromethanesulfonate; sodium hydride; 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;

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

upstream raw materials:

2-(4-{(R)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-[[(E)-5-(tert-butyl-diphenyl-silanyloxy)-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

N-[2-(6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-1-hydroxymethyl-ethyl]-N-[5-(tert-butyl-diphenyl-silanyloxy)-pent-3-enyl]-4-methyl-benzenesulfonamide

Downstream 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

(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