(E)-(S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-14-oxo-4-(toluene-4-sulfonyl)-1-oxa-4-aza-cyclotetradec-7-ene-10,10-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: (E)-(S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-14-oxo-4-(toluene-4-sulfonyl)-1-oxa-4-aza-cyclotetradec-7-ene-10,10-dicarboxylic acid dimethyl ester
• CAS No.: 295337-59-6
• Molecular Formula: C₃₇H₄₉NO₁₁S
• Molecular Weight: 715.862
• Mol file: 295337-59-6.mol

Synonyms:(E)-(S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-14-oxo-4-(toluene-4-sulfonyl)-1-oxa-4-aza-cyclotetradec-7-ene-10,10-dicarboxylic acid dimethyl ester

Chemical Property of (E)-(S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-14-oxo-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)-(S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-14-oxo-4-(toluene-4-sulfonyl)-1-oxa-4-aza-cyclotetradec-7-ene-10,10-dicarboxylic acid dimethyl ester

There total 9 articles about (E)-(S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-14-oxo-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: 90.0%

2-Methoxycarbonyl-hexanedioic acid 6-{(S)-3-(6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-[((E)-5-chloro-pent-3-enyl)-(toluene-4-sulfonyl)-amino]-propyl} ester 1-methyl ester (295337-57-4) → (E)-(S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-14-oxo-4-(toluene-4-sulfonyl)-1-oxa-4-aza-cyclotetradec-7-ene-10,10-dicarboxylic acid dimethyl ester (295337-59-6)

Guidance literature:

With caesium carbonate; In acetonitrile; at 70 ℃; for 30h;

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

Reference yield:

2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran (194861-23-9) → (E)-(S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-14-oxo-4-(toluene-4-sulfonyl)-1-oxa-4-aza-cyclotetradec-7-ene-10,10-dicarboxylic acid dimethyl ester (295337-59-6)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: dmap; 1,1'-carbonyldiimidazole / tetrahydrofuran; diethyl ether / 13 h / 20 °C

4: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 3.5 h / 20 °C

5: caesium carbonate / acetonitrile / 30 h / 70 °C

With dmap; lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; caesium carbonate; triphenylphosphine; 1,1'-carbonyldiimidazole; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; 1,2-dichloro-ethane; acetonitrile; 1: Etherification / 2: Reduction / 3: Condensation / 4: Mitsunobu reaction / 5: Cyclization;

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

Reference yield:

methoxy-5-(methoxycarbonyl)-6-oxohexanoic acid (182884-47-5) → (E)-(S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-14-oxo-4-(toluene-4-sulfonyl)-1-oxa-4-aza-cyclotetradec-7-ene-10,10-dicarboxylic acid dimethyl ester (295337-59-6)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap; 1,1'-carbonyldiimidazole / tetrahydrofuran; diethyl ether / 13 h / 20 °C

2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 3.5 h / 20 °C

3: caesium carbonate / acetonitrile / 30 h / 70 °C

With dmap; caesium carbonate; triphenylphosphine; 1,1'-carbonyldiimidazole; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; acetonitrile; 1: Condensation / 2: Mitsunobu reaction / 3: Cyclization;

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

upstream raw materials:

2-Methoxycarbonyl-hexanedioic acid 6-{(S)-3-(6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-[((E)-5-chloro-pent-3-enyl)-(toluene-4-sulfonyl)-amino]-propyl} ester 1-methyl ester

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

2-(4-Hydroxy-butyl)-malonic acid dimethyl ester

methoxy-5-(methoxycarbonyl)-6-oxohexanoic acid