(S)-2-[(5S,6S)-6-((1E,5E)-(3S,4R)-4-Hydroxy-1,3,5-trimethyl-hepta-1,5-dienyl)-5-methyl-5,6-dihydro-4H-pyran-2-yl]-2-(4-methoxy-benzyloxy)-butyric acid benzotriazol-1-yl ester

Base Information

• Chemical Name: (S)-2-[(5S,6S)-6-((1E,5E)-(3S,4R)-4-Hydroxy-1,3,5-trimethyl-hepta-1,5-dienyl)-5-methyl-5,6-dihydro-4H-pyran-2-yl]-2-(4-methoxy-benzyloxy)-butyric acid benzotriazol-1-yl ester
• CAS No.: 186522-66-7
• Molecular Formula: C₃₄H₄₃N₃O₆
• Molecular Weight: 589.732
• Mol file: 186522-66-7.mol

Synonyms:(S)-2-[(5S,6S)-6-((1E,5E)-(3S,4R)-4-Hydroxy-1,3,5-trimethyl-hepta-1,5-dienyl)-5-methyl-5,6-dihydro-4H-pyran-2-yl]-2-(4-methoxy-benzyloxy)-butyric acid benzotriazol-1-yl ester

Chemical Property of (S)-2-[(5S,6S)-6-((1E,5E)-(3S,4R)-4-Hydroxy-1,3,5-trimethyl-hepta-1,5-dienyl)-5-methyl-5,6-dihydro-4H-pyran-2-yl]-2-(4-methoxy-benzyloxy)-butyric acid benzotriazol-1-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(5S,6S)-6-((1E,5E)-(3S,4R)-4-Hydroxy-1,3,5-trimethyl-hepta-1,5-dienyl)-5-methyl-5,6-dihydro-4H-pyran-2-yl]-2-(4-methoxy-benzyloxy)-butyric acid benzotriazol-1-yl ester

There total 3 articles about (S)-2-[(5S,6S)-6-((1E,5E)-(3S,4R)-4-Hydroxy-1,3,5-trimethyl-hepta-1,5-dienyl)-5-methyl-5,6-dihydro-4H-pyran-2-yl]-2-(4-methoxy-benzyloxy)-butyric acid benzotriazol-1-yl 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:

(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (56602-33-6) + (S)-2-[(5S,6S)-6-((1E,5E)-(3S,4R)-4-Hydroxy-1,3,5-trimethyl-hepta-1,5-dienyl)-5-methyl-5,6-dihydro-4H-pyran-2-yl]-2-(4-methoxy-benzyloxy)-butyric acid → (S)-2-[(5S,6S)-6-((1E,5E)-(3S,4R)-4-Hydroxy-1,3,5-trimethyl-hepta-1,5-dienyl)-5-methyl-5,6-dihydro-4H-pyran-2-yl]-2-(4-methoxy-benzyloxy)-butyric acid benzotriazol-1-yl ester (186522-66-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; Yield given;

DOI:10.1016/S0040-4039(97)82960-7

Reference yield:

(S)-2-[(5S,6S)-6-((1E,5E)-(3S,4R)-4-Hydroxy-1,3,5-trimethyl-hepta-1,5-dienyl)-5-methyl-5,6-dihydro-4H-pyran-2-yl]-2-(4-methoxy-benzyloxy)-butyric acid methyl ester (186522-64-5) → (S)-2-[(5S,6S)-6-((1E,5E)-(3S,4R)-4-Hydroxy-1,3,5-trimethyl-hepta-1,5-dienyl)-5-methyl-5,6-dihydro-4H-pyran-2-yl]-2-(4-methoxy-benzyloxy)-butyric acid benzotriazol-1-yl ester (186522-66-7)

Guidance literature:

Multi-step reaction with 2 steps

1: EtSLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / Ambient temperature

2: iPr₂EtN / CH₂Cl₂

With lithium thioethoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1016/S0040-4039(97)82960-7

Reference yield:

(S)-2-{(5S,6S)-6-[(1E,5E)-(3S,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,3,5-trimethyl-hepta-1,5-dienyl]-5-methyl-5,6-dihydro-4H-pyran-2-yl}-2-(4-methoxy-benzyloxy)-butyric acid methyl ester (180285-55-6) → (S)-2-[(5S,6S)-6-((1E,5E)-(3S,4R)-4-Hydroxy-1,3,5-trimethyl-hepta-1,5-dienyl)-5-methyl-5,6-dihydro-4H-pyran-2-yl]-2-(4-methoxy-benzyloxy)-butyric acid benzotriazol-1-yl ester (186522-66-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / nBu₄NF / dimethylformamide / 48 h / Ambient temperature

2: EtSLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / Ambient temperature

3: iPr₂EtN / CH₂Cl₂

With tetrabutyl ammonium fluoride; lithium thioethoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)82960-7

upstream raw materials:

(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

(S)-2-[(5S,6S)-6-((1E,5E)-(3S,4R)-4-Hydroxy-1,3,5-trimethyl-hepta-1,5-dienyl)-5-methyl-5,6-dihydro-4H-pyran-2-yl]-2-(4-methoxy-benzyloxy)-butyric acid methyl ester

(S)-2-{(5S,6S)-6-[(1E,5E)-(3S,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,3,5-trimethyl-hepta-1,5-dienyl]-5-methyl-5,6-dihydro-4H-pyran-2-yl}-2-(4-methoxy-benzyloxy)-butyric acid methyl ester

Refernces

• 1、 Hale, Karl J.,Cai, Jiaqiang,Delisser, Vern M.. "Asymmetric synthesis of the C(1)-C(47) backbone of antitumour antibiotic A83586C". . p. 9345 - 9348. Retrieved 2007/10/03.