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

Base Information

• Chemical Name: 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
• CAS No.: 877374-65-7
• Molecular Formula: C₄₂H₇₂O₅Si₂
• Molecular Weight: 713.202

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 23 articles about 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 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: 89.0%

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) + methylmagnesium chloride (676-58-4) → 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)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃; for 14h;

DOI:10.1021/ja056334b

Reference yield:

(2-iodomethyl-allyloxy)-triisopropyl-silane (877374-30-6) → 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)

Guidance literature:

Multi-step reaction with 16 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

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

Reference yield:

(2R,8R,9R)-8-benzyloxy-9-benzyloxymethyl-8-methyl-4-triisopropylsilanyloxymethyl-2,3,6,7,8,9-hexahydro-oxonine-2-carbaldehyde (877374-60-2) → 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)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 0.658 g / toluene / 80 °C

2.1: 98 percent / diisobutylaluminum hydride / heptane; diethyl ether / 0.5 h / -78 °C

3.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 40 h / -78 °C

4.1: 61 percent / Na / liquid ammonia; tetrahydrofuran / -78 °C

5.1: 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves; tetrapropylammonium perruthenate / CH₂Cl₂ / 0.25 h / 20 °C

6.1: 76 percent / CH₂Cl₂ / 1 h / Heating

7.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

8.1: 85 percent / pyridinium p-toluenesulfonate / methanol / 0.25 h / 20 °C

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

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

10.2: tetrahydrofuran / 0.75 h / -78 °C

11.1: benzene / 12 h / 20 °C

11.2: 0.127 g / diphenyldisulfide / benzene / 1 h

12.1: 89 percent / tetrahydrofuran / 14 h / 0 - 20 °C

With pyridine; 2,6-dimethylpyridine; tetrapropylammonium perruthennate; 4 A molecular sieve; potassium tert-butylate; sodium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; diethyl ether; n-heptane; dichloromethane; ammonia; toluene; benzene; 1.1: Wittig reaction / 6.1: Wittig reaction / 10.2: Wittig reaction;

DOI:10.1021/ja056334b

upstream raw materials:

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

methylmagnesium chloride

(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

Downstream raw materials:

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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