acetic acid 1-{4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-5,10-dien-3-yl}-1-methyl-ethyl ester

Base Information

• Chemical Name: acetic acid 1-{4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-5,10-dien-3-yl}-1-methyl-ethyl ester
• CAS No.: 877374-50-0
• Molecular Formula: C₄₄H₇₄O₆Si₂
• Molecular Weight: 755.239

Synonyms:acetic acid 1-{4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-5,10-dien-3-yl}-1-methyl-ethyl ester

Chemical Property of acetic acid 1-{4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-5,10-dien-3-yl}-1-methyl-ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of acetic acid 1-{4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-5,10-dien-3-yl}-1-methyl-ethyl ester

There total 25 articles about acetic acid 1-{4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-5,10-dien-3-yl}-1-methyl-ethyl 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: 54.0%

2-{4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.02,7]pentadeca-5,10-dien-3-yl}propan-2-ol (877374-65-7) + acetic anhydride (108-24-7) → acetic acid 1-{4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.02,7]pentadeca-5,10-dien-3-yl}-1-methyl-ethyl ester (877374-50-0)

Guidance literature:

2-{4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-5,10-dien-3-yl}propan-2-ol; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 1h;

acetic anhydride; In tetrahydrofuran; at 4 ℃; for 13h;

DOI:10.1021/ja056334b

Reference yield:

(2-chloromethyl-allyloxy)-triisopropyl-silane (877374-59-9) → acetic acid 1-{4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.02,7]pentadeca-5,10-dien-3-yl}-1-methyl-ethyl ester (877374-50-0)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 90 percent / NaI / acetone / 12 h / 20 °C

2.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

2.2: 94 percent / tetrahydrofuran; toluene / 1.25 h / -78 - -45 °C

3.1: 76 percent / lithium borohydride / methanol; diethyl ether / 1 h / 0 °C

4.1: Cl₂(Cy₃P)(sIMes)Ru=ChPh / hexane / 1 h / Heating

4.2: 88 percent / phenyl disulfide / benzene / 2 h / 20 °C / UV-irradiation

5.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2 h / 20 °C

6.1: 0.658 g / toluene / 80 °C

7.1: 98 percent / diisobutylaluminum hydride / heptane; diethyl ether / 0.5 h / -78 °C

8.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 40 h / -78 °C

9.1: 61 percent / Na / liquid ammonia; tetrahydrofuran / -78 °C

10.1: 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves; tetrapropylammonium perruthenate / CH₂Cl₂ / 0.25 h / 20 °C

11.1: 76 percent / CH₂Cl₂ / 1 h / Heating

12.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

13.1: 85 percent / pyridinium p-toluenesulfonate / methanol / 0.25 h / 20 °C

14.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

15.1: potassium tert-butoxide / tetrahydrofuran / 1 h / -78 °C

15.2: tetrahydrofuran / 0.75 h / -78 °C

16.1: benzene / 12 h / 20 °C

16.2: 0.127 g / diphenyldisulfide / benzene / 1 h

17.1: 89 percent / tetrahydrofuran / 14 h / 0 - 20 °C

18.1: NaHMDS / tetrahydrofuran / 1 h / 0 °C

18.2: 54 percent / tetrahydrofuran / 13 h / 4 °C

With pyridine; 2,6-dimethylpyridine; lithium borohydride; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; tetrapropylammonium perruthennate; 4 A molecular sieve; potassium tert-butylate; sodium hexamethyldisilazane; sodium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; 4-methylmorpholine N-oxide; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; hexane; n-heptane; dichloromethane; ammonia; acetone; toluene; benzene; 4.1: Diels-Alder reaction / 6.1: Wittig reaction / 11.1: Wittig reaction / 15.2: Wittig reaction;

DOI:10.1021/ja056334b

Reference yield:

(2-iodomethyl-allyloxy)-triisopropyl-silane (877374-30-6) → acetic acid 1-{4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.02,7]pentadeca-5,10-dien-3-yl}-1-methyl-ethyl ester (877374-50-0)

Guidance literature:

Multi-step reaction with 17 steps

1.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

1.2: 94 percent / tetrahydrofuran; toluene / 1.25 h / -78 - -45 °C

2.1: 76 percent / lithium borohydride / methanol; diethyl ether / 1 h / 0 °C

3.1: Cl₂(Cy₃P)(sIMes)Ru=ChPh / hexane / 1 h / Heating

3.2: 88 percent / phenyl disulfide / benzene / 2 h / 20 °C / UV-irradiation

4.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2 h / 20 °C

5.1: 0.658 g / toluene / 80 °C

6.1: 98 percent / diisobutylaluminum hydride / heptane; diethyl ether / 0.5 h / -78 °C

7.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 40 h / -78 °C

8.1: 61 percent / Na / liquid ammonia; tetrahydrofuran / -78 °C

9.1: 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves; tetrapropylammonium perruthenate / CH₂Cl₂ / 0.25 h / 20 °C

10.1: 76 percent / CH₂Cl₂ / 1 h / Heating

11.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

12.1: 85 percent / pyridinium p-toluenesulfonate / methanol / 0.25 h / 20 °C

13.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

14.1: potassium tert-butoxide / tetrahydrofuran / 1 h / -78 °C

14.2: tetrahydrofuran / 0.75 h / -78 °C

15.1: benzene / 12 h / 20 °C

15.2: 0.127 g / diphenyldisulfide / benzene / 1 h

16.1: 89 percent / tetrahydrofuran / 14 h / 0 - 20 °C

17.1: NaHMDS / tetrahydrofuran / 1 h / 0 °C

17.2: 54 percent / tetrahydrofuran / 13 h / 4 °C

With pyridine; 2,6-dimethylpyridine; lithium borohydride; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; tetrapropylammonium perruthennate; 4 A molecular sieve; potassium tert-butylate; sodium hexamethyldisilazane; sodium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; diethyl ether; hexane; n-heptane; dichloromethane; ammonia; toluene; benzene; 3.1: Diels-Alder reaction / 5.1: Wittig reaction / 10.1: Wittig reaction / 14.2: Wittig reaction;

DOI:10.1021/ja056334b

upstream raw materials:

2-{4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-5,10-dien-3-yl}propan-2-ol

acetic anhydride

(2-chloromethyl-allyloxy)-triisopropyl-silane

(2-iodomethyl-allyloxy)-triisopropyl-silane

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