4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethoxymethyl ester

Base Information

• Chemical Name: 4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethoxymethyl ester
• CAS No.: 349539-64-6
• Molecular Formula: C₅₁H₇₈O₁₁Si
• Molecular Weight: 895.259

Synonyms:4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethoxymethyl ester

Chemical Property of 4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethoxymethyl ester

Chemical Property:

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Technology Process of 4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethoxymethyl ester

There total 6 articles about 4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethoxymethyl 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: 64.0%

(diphenoxy-phosphoryl)-acetic acid 2-trimethylsilanyl-ethoxymethyl ester (349539-82-8) + {(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-10-(4-Methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-acetaldehyde → 4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethoxymethyl ester (349539-64-6)

Guidance literature:

With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1016/S0040-4039(01)00436-1

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → 4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethoxymethyl ester (349539-64-6)

Guidance literature:

Multi-step reaction with 4 steps

1: PPTS / CH₂Cl₂

2: 76 percent / TBAF / tetrahydrofuran

3: Dess-Martin reagent / CH₂Cl₂

4: 64 percent / KN(TMS)2; 18-crown-6 / tetrahydrofuran / 0.5 h / -78 °C

With 18-crown-6 ether; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 3: Dess-Martin oxidation / 4: Ando's modified Horner-Emmons reaction;

DOI:10.1016/S0040-4039(01)00436-1

Reference yield:

(2-trimethylsilanyl-ethoxy)-methanol → 4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethoxymethyl ester (349539-64-6)

Guidance literature:

Multi-step reaction with 2 steps

1: DCC; DMAP / CH₂Cl₂

2: 64 percent / KN(TMS)2; 18-crown-6 / tetrahydrofuran / 0.5 h / -78 °C

With dmap; 18-crown-6 ether; potassium hexamethylsilazane; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 2: Ando's modified Horner-Emmons reaction;

DOI:10.1016/S0040-4039(01)00436-1

upstream raw materials:

(diphenoxy-phosphoryl)-acetic acid 2-trimethylsilanyl-ethoxymethyl ester

3,4-dihydro-2H-pyran

2-{(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-10-(4-Methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-ethanol

(1E,6E)-(3S,4S,8S,12S)-13-{(2R,6R)-6-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-4-(4-methoxy-benzyloxy)-8-methoxymethoxy-12-methyl-1-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-10-methylene-trideca-1,6-dien-3-ol

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