4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-5,10-diene-3-carboxylic acid isopropyl ester

Base Information

• Chemical Name: 4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-5,10-diene-3-carboxylic acid isopropyl ester
• CAS No.: 877374-49-7
• Molecular Formula: C₄₃H₇₂O₆Si₂
• Molecular Weight: 741.212

Synonyms:4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-5,10-diene-3-carboxylic acid isopropyl ester

Chemical Property of 4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-5,10-diene-3-carboxylic acid isopropyl ester

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of 4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-5,10-diene-3-carboxylic acid isopropyl ester

There total 23 articles about 4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-5,10-diene-3-carboxylic acid isopropyl 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:

3-{(2R,3R,9R)-9-[4-benzyloxy-2-methyl-buta-1,3-dienyl]-3-methyl-3-triethylsilanyloxy-7-triisopropylsilanyloxymethyl-2,3,4,5,8,9-hexahydro-oxonin-2-yl}acrylic acid isopropyl ester → 4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.02,7]pentadeca-5,10-diene-3-carboxylic acid isopropyl ester (877374-49-7)

Guidance literature:

3-{(2R,3R,9R)-9-[4-benzyloxy-2-methyl-buta-1,3-dienyl]-3-methyl-3-triethylsilanyloxy-7-triisopropylsilanyloxymethyl-2,3,4,5,8,9-hexahydro-oxonin-2-yl}acrylic acid isopropyl ester; In benzene; at 20 ℃; for 12h;

With diphenyldisulfane; In benzene; for 1h;

DOI:10.1021/ja056334b

Reference yield:

(2-chloromethyl-allyloxy)-triisopropyl-silane (877374-59-9) → 4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.02,7]pentadeca-5,10-diene-3-carboxylic acid isopropyl ester (877374-49-7)

Guidance literature:

Multi-step reaction with 16 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

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) → 4-benzyloxy-6,14-dimethyl-14-triethylsilanyloxy-10-triisopropylsilanyloxymethyl-15-oxatricyclo[6.6.1.02,7]pentadeca-5,10-diene-3-carboxylic acid isopropyl ester (877374-49-7)

Guidance literature:

Multi-step reaction with 15 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

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-chloromethyl-allyloxy)-triisopropyl-silane

(2-iodomethyl-allyloxy)-triisopropyl-silane

(2R,8R,9R)-8-benzyloxy-9-benzyloxymethyl-8-methyl-4-triisopropylsilanyloxymethyl-2,3,6,7,8,9-hexahydro-oxonine-2-carbaldehyde

(2S,3R,9R)-3-hydroxy-3-methyl-9-(2-methyl-3-triethylsilanyloxy-propenyl)-7-triisopropylsilanyloxymethyl-2,3,4,5,8,9-hexahydro-oxonine-2-carbaldehyde

Downstream 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 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

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