2-{2-(3,4-dimethoxy-benzyloxy)-6-hydroxy-1-[2-(4-methoxy-benzyloxy)-ethyl]-hex-4-enyloxy}-N,N-dimethyl-acetamide

Base Information

• Chemical Name: 2-{2-(3,4-dimethoxy-benzyloxy)-6-hydroxy-1-[2-(4-methoxy-benzyloxy)-ethyl]-hex-4-enyloxy}-N,N-dimethyl-acetamide
• CAS No.: 597535-48-3
• Molecular Formula: C₂₉H₄₁NO₈
• Molecular Weight: 531.646
• Mol file: 597535-48-3.mol

Synonyms:2-{2-(3,4-dimethoxy-benzyloxy)-6-hydroxy-1-[2-(4-methoxy-benzyloxy)-ethyl]-hex-4-enyloxy}-N,N-dimethyl-acetamide

Chemical Property of 2-{2-(3,4-dimethoxy-benzyloxy)-6-hydroxy-1-[2-(4-methoxy-benzyloxy)-ethyl]-hex-4-enyloxy}-N,N-dimethyl-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{2-(3,4-dimethoxy-benzyloxy)-6-hydroxy-1-[2-(4-methoxy-benzyloxy)-ethyl]-hex-4-enyloxy}-N,N-dimethyl-acetamide

There total 9 articles about 2-{2-(3,4-dimethoxy-benzyloxy)-6-hydroxy-1-[2-(4-methoxy-benzyloxy)-ethyl]-hex-4-enyloxy}-N,N-dimethyl-acetamide 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: 95.0%

2-[2-(3,4-dimethoxy-benzyloxy)-1-[2-(4-methoxy-benzyloxy)-ethyl]-6-(tetrahydro-pyran-2-yloxy)-hex-4-enyloxy]-N,N-dimethyl-acetamide (597535-29-0) → 2-{2-(3,4-dimethoxy-benzyloxy)-6-hydroxy-1-[2-(4-methoxy-benzyloxy)-ethyl]-hex-4-enyloxy}-N,N-dimethyl-acetamide (597535-48-3)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; at 20 ℃; for 1h;

DOI:10.1021/ja035538u

Reference yield:

(S)-1-[(R)-oxiran-2-yl]prop-2-enol (100017-22-9) → 2-{2-(3,4-dimethoxy-benzyloxy)-6-hydroxy-1-[2-(4-methoxy-benzyloxy)-ethyl]-hex-4-enyloxy}-N,N-dimethyl-acetamide (597535-48-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 90 percent / tetrahydrofuran / 2.5 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 90 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.1: NaH / tetrahydrofuran; dimethylformamide / 0.5 h / 0 °C

3.2: 92 percent / tetrahydrofuran; dimethylformamide / 1.5 h / 20 °C

4.1: 100 percent / H₂; pyridine / Lindlar catalyst / ethyl acetate / 3 h / 20 °C

5.1: 83 percent / 9-BBN / tetrahydrofuran / 0 - 20 °C

6.1: NaH / tetrahydrofuran; dimethylformamide / 0.5 h / 0 °C

6.2: 94 percent / tetrahydrofuran; dimethylformamide / 13 h / 20 °C

7.1: 76 percent / TBAF; DMPU; 4A molecular sieves / tetrahydrofuran / 5 h / 80 °C

8.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

8.2: 99 percent / tetrahydrofuran / 8 h / 20 °C

9.1: 95 percent / p-toluenesulfonic acid / ethanol / 1 h / 20 °C

With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; toluene-4-sulfonic acid; Lindlar's catalyst; In tetrahydrofuran; ethanol; hexane; ethyl acetate; N,N-dimethyl-formamide; 2.2: Yamaguchi reaction;

DOI:10.1021/ja035538u

Reference yield:

Trimethyl-[2-((S)-(R)-1-oxiranyl-allyloxymethoxy)-ethyl]-silane (597535-17-6) → 2-{2-(3,4-dimethoxy-benzyloxy)-6-hydroxy-1-[2-(4-methoxy-benzyloxy)-ethyl]-hex-4-enyloxy}-N,N-dimethyl-acetamide (597535-48-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 90 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.1: NaH / tetrahydrofuran; dimethylformamide / 0.5 h / 0 °C

2.2: 92 percent / tetrahydrofuran; dimethylformamide / 1.5 h / 20 °C

3.1: 100 percent / H₂; pyridine / Lindlar catalyst / ethyl acetate / 3 h / 20 °C

4.1: 83 percent / 9-BBN / tetrahydrofuran / 0 - 20 °C

5.1: NaH / tetrahydrofuran; dimethylformamide / 0.5 h / 0 °C

5.2: 94 percent / tetrahydrofuran; dimethylformamide / 13 h / 20 °C

6.1: 76 percent / TBAF; DMPU; 4A molecular sieves / tetrahydrofuran / 5 h / 80 °C

7.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

7.2: 99 percent / tetrahydrofuran / 8 h / 20 °C

8.1: 95 percent / p-toluenesulfonic acid / ethanol / 1 h / 20 °C

With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; toluene-4-sulfonic acid; Lindlar's catalyst; In tetrahydrofuran; ethanol; hexane; ethyl acetate; N,N-dimethyl-formamide; 1.2: Yamaguchi reaction;

DOI:10.1021/ja035538u

upstream raw materials:

2-[2-(3,4-dimethoxy-benzyloxy)-1-[2-(4-methoxy-benzyloxy)-ethyl]-6-(tetrahydro-pyran-2-yloxy)-hex-4-enyloxy]-N,N-dimethyl-acetamide

(S)-1-[(R)-oxiran-2-yl]prop-2-enol

Trimethyl-[2-((S)-(R)-1-oxiranyl-allyloxymethoxy)-ethyl]-silane

(3S,4R)-8-(Tetrahydro-pyran-2-yloxy)-3-(2-trimethylsilanyl-ethoxymethoxy)-oct-1-en-6-yn-4-ol

Downstream raw materials:

2-{6-chloro-2-(3,4-dimethoxy-benzyloxy)-1-[2-(4-methoxy-benzyloxy)-ethyl]-hex-4-enyloxy}-N,N-dimethyl-acetamide