2,2-Dimethyl-propionic acid (S)-2-(4-methoxy-benzyloxy)-2-((4S,6R,9R,10R)-9-phenoxy-10-triethylsilanyloxy-5-oxa-tricyclo[8.3.0.0^4,6]trideca-1⁽¹³⁾,11-diene-2,7-diyn-4-yl)-ethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (S)-2-(4-methoxy-benzyloxy)-2-((4S,6R,9R,10R)-9-phenoxy-10-triethylsilanyloxy-5-oxa-tricyclo[8.3.0.0^4,6]trideca-1⁽¹³⁾,11-diene-2,7-diyn-4-yl)-ethyl ester
• CAS No.: 791072-87-2
• Molecular Formula: C₃₉H₄₆O₇Si
• Molecular Weight: 654.876

Synonyms:2,2-Dimethyl-propionic acid (S)-2-(4-methoxy-benzyloxy)-2-((4S,6R,9R,10R)-9-phenoxy-10-triethylsilanyloxy-5-oxa-tricyclo[8.3.0.0^4,6]trideca-1⁽¹³⁾,11-diene-2,7-diyn-4-yl)-ethyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (S)-2-(4-methoxy-benzyloxy)-2-((4S,6R,9R,10R)-9-phenoxy-10-triethylsilanyloxy-5-oxa-tricyclo[8.3.0.0^4,6]trideca-1⁽¹³⁾,11-diene-2,7-diyn-4-yl)-ethyl ester

Chemical Property:

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Technology Process of 2,2-Dimethyl-propionic acid (S)-2-(4-methoxy-benzyloxy)-2-((4S,6R,9R,10R)-9-phenoxy-10-triethylsilanyloxy-5-oxa-tricyclo[8.3.0.0^4,6]trideca-1⁽¹³⁾,11-diene-2,7-diyn-4-yl)-ethyl ester

There total 15 articles about 2,2-Dimethyl-propionic acid (S)-2-(4-methoxy-benzyloxy)-2-((4S,6R,9R,10R)-9-phenoxy-10-triethylsilanyloxy-5-oxa-tricyclo[8.3.0.0^4,6]trideca-1⁽¹³⁾,11-diene-2,7-diyn-4-yl)-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:

2,2-Dimethyl-propionic acid (S)-2-(4-methoxy-benzyloxy)-2-[(4S,6R,9R,10R,12R)-12-(2-nitro-phenylselanyl)-9-phenoxy-10-triethylsilanyloxy-5-oxa-tricyclo[8.3.0.04,6]tridec-1(13)-ene-2,7-diyn-4-yl]-ethyl ester → 2,2-Dimethyl-propionic acid (S)-2-(4-methoxy-benzyloxy)-2-((4S,6R,9R,10R)-9-phenoxy-10-triethylsilanyloxy-5-oxa-tricyclo[8.3.0.04,6]trideca-1(13),11-diene-2,7-diyn-4-yl)-ethyl ester (791072-87-2)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ol048494i

Reference yield:

triethylsilyl chloride (994-30-9) → 2,2-Dimethyl-propionic acid (S)-2-(4-methoxy-benzyloxy)-2-((4S,6R,9R,10R)-9-phenoxy-10-triethylsilanyloxy-5-oxa-tricyclo[8.3.0.04,6]trideca-1(13),11-diene-2,7-diyn-4-yl)-ethyl ester (791072-87-2)

Guidance literature:

Multi-step reaction with 12 steps

1: imidazole / dimethylformamide / 1.17 h / 50 °C

2: 1.45 g / HN(TMS)2; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

3: iPr₂NEt; CuI / Pd₂(dba)3*CHCl₃ / dimethylformamide / 1 h / 20 °C

4: 1.79 g / TBAF / tetrahydrofuran / 1 h / -60 °C

5: 88 percent / ZnBr₂ / CH₂Cl₂ / 2.5 h / 20 °C

6: 71 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

7: 98 percent / CeCl₃; n-BuLi; HN(TMS)2 / tetrahydrofuran; hexane / -25 - 0 °C

8: 78 percent / DMAP; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

9: 88 percent / Me₃BBr / CH₂Cl₂ / 0.5 h / -90 °C

10: 86 percent / TBAF / tetrahydrofuran / 1 h / -50 °C

11: n-Bu₃P / tetrahydrofuran / 0.75 h / 20 °C

12: 5.1 mg / aq. H₂O₂ / tetrahydrofuran / 20 °C

With 1H-imidazole; dmap; copper(l) iodide; n-butyllithium; cerium(III) chloride; tributylphosphine; tetrabutyl ammonium fluoride; dihydrogen peroxide; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; zinc dibromide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 3: Sonogashira coupling / 6: Dess-Martin oxidation;

DOI:10.1021/ol048494i

Reference yield:

(2S,3S,6S)-2-Ethynyl-4-iodo-6-methoxymethoxy-1-oxa-spiro[2.4]hept-4-ene (791072-89-4) → 2,2-Dimethyl-propionic acid (S)-2-(4-methoxy-benzyloxy)-2-((4S,6R,9R,10R)-9-phenoxy-10-triethylsilanyloxy-5-oxa-tricyclo[8.3.0.04,6]trideca-1(13),11-diene-2,7-diyn-4-yl)-ethyl ester (791072-87-2)

Guidance literature:

Multi-step reaction with 13 steps

1: 83 percent / CsF / dimethylformamide / 4 h / 80 °C

2: imidazole / dimethylformamide / 1.17 h / 50 °C

3: 1.45 g / HN(TMS)2; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

4: iPr₂NEt; CuI / Pd₂(dba)3*CHCl₃ / dimethylformamide / 1 h / 20 °C

5: 1.79 g / TBAF / tetrahydrofuran / 1 h / -60 °C

6: 88 percent / ZnBr₂ / CH₂Cl₂ / 2.5 h / 20 °C

7: 71 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

8: 98 percent / CeCl₃; n-BuLi; HN(TMS)2 / tetrahydrofuran; hexane / -25 - 0 °C

9: 78 percent / DMAP; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

10: 88 percent / Me₃BBr / CH₂Cl₂ / 0.5 h / -90 °C

11: 86 percent / TBAF / tetrahydrofuran / 1 h / -50 °C

12: n-Bu₃P / tetrahydrofuran / 0.75 h / 20 °C

13: 5.1 mg / aq. H₂O₂ / tetrahydrofuran / 20 °C

With 1H-imidazole; dmap; copper(l) iodide; n-butyllithium; cerium(III) chloride; tributylphosphine; tetrabutyl ammonium fluoride; dihydrogen peroxide; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; cesium fluoride; 1,1,1,3,3,3-hexamethyl-disilazane; zinc dibromide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 4: Sonogashira coupling / 7: Dess-Martin oxidation;

DOI:10.1021/ol048494i

upstream raw materials:

triethylsilyl chloride

(2S,3S,6S)-2-Ethynyl-4-iodo-6-methoxymethoxy-1-oxa-spiro[2.4]hept-4-ene

(1S,4S)-2-Iodo-4-methoxymethoxy-1-((R)-1-phenoxy-prop-2-ynyl)-cyclopent-2-enol

[(R)-1-((1S,4S)-2-Iodo-4-methoxymethoxy-1-triethylsilanyloxy-cyclopent-2-enyl)-3-trimethylsilanyl-prop-2-ynyloxy]-benzene

Downstream raw materials:

C₃₉H₄₆O₆Si

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