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

Base Information

• Chemical Name: (1S,4S)-2-Iodo-4-methoxymethoxy-1-((R)-1-phenoxy-prop-2-ynyl)-cyclopent-2-enol
• CAS No.: 791072-90-7
• Molecular Formula: C₁₆H₁₇IO₄
• Molecular Weight: 400.213
• Mol file: 791072-90-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (1S,4S)-2-Iodo-4-methoxymethoxy-1-((R)-1-phenoxy-prop-2-ynyl)-cyclopent-2-enol 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: 83.0%

phenol (108-95-2,27073-41-2) + (2S,3S,6S)-2-Ethynyl-4-iodo-6-methoxymethoxy-1-oxa-spiro[2.4]hept-4-ene (791072-89-4) → (1S,4S)-2-Iodo-4-methoxymethoxy-1-((R)-1-phenoxy-prop-2-ynyl)-cyclopent-2-enol (791072-90-7)

Guidance literature:

With cesium fluoride; In N,N-dimethyl-formamide; at 80 ℃; for 4h;

DOI:10.1021/ol048494i

Reference yield:

(1S,4S)-2-Iodo-4-methoxymethoxy-1-((R)-1-phenoxy-prop-2-ynyl)-cyclopent-2-enol (791072-90-7) → C39H48O7Si

Guidance literature:

Multi-step reaction with 13 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

13: 10 percent / Cp₂TiCl / tetrahydrofuran / 1 h / 0 °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; bis(cyclopentadienyl)titanium (III) chloride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 3: Sonogashira coupling / 6: Dess-Martin oxidation;

DOI:10.1021/ol048494i

Reference yield:

(1S,4S)-2-Iodo-4-methoxymethoxy-1-((R)-1-phenoxy-prop-2-ynyl)-cyclopent-2-enol (791072-90-7) → 2,2-Dimethyl-propionic acid (S)-2-((4S,6R,9R,10R,12S)-12-hydroxy-9-phenoxy-10-triethylsilanyloxy-5-oxa-tricyclo[8.3.0.04,6]tridec-1(13)-ene-2,7-diyn-4-yl)-2-(4-methoxy-benzyloxy)-ethyl ester (791072-98-5)

Guidance literature:

Multi-step reaction with 10 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

With 1H-imidazole; dmap; copper(l) iodide; n-butyllithium; cerium(III) chloride; tetrabutyl ammonium fluoride; 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

upstream raw materials:

phenol

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

Downstream raw materials:

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

C₃₉H₄₆O₆Si

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

2,2-Dimethyl-propionic acid (S)-2-((4S,6R,9R,10R,12S)-12-hydroxy-9-phenoxy-10-triethylsilanyloxy-5-oxa-tricyclo[8.3.0.0^4,6]tridec-1⁽¹³⁾-ene-2,7-diyn-4-yl)-2-(4-methoxy-benzyloxy)-ethyl ester