2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-((3R,5S)-5-tert-butyldimethylsilyloxy-3-(triethylsilyloxy)cyclopent-1-enyl)ethanone

Base Information

Chemical Name:2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-((3R,5S)-5-tert-butyldimethylsilyloxy-3-(triethylsilyloxy)cyclopent-1-enyl)ethanone
CAS No.:953786-58-8
Molecular Formula:C₃₄H₅₁IO₆Si₂
Molecular Weight:738.851
Hs Code.:

Synonyms:2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-((3R,5S)-5-tert-butyldimethylsilyloxy-3-(triethylsilyloxy)cyclopent-1-enyl)ethanone

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Chemical Property of 2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-((3R,5S)-5-tert-butyldimethylsilyloxy-3-(triethylsilyloxy)cyclopent-1-enyl)ethanone

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Technology Process of 2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-((3R,5S)-5-tert-butyldimethylsilyloxy-3-(triethylsilyloxy)cyclopent-1-enyl)ethanone

There total 12 articles about 2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-((3R,5S)-5-tert-butyldimethylsilyloxy-3-(triethylsilyloxy)cyclopent-1-enyl)ethanone 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: 63.0%

: 953786-57-7
(1S,4R)-1-(tert-butyldimethylsilyloxy)-4-(triethylsilyloxy)-2-iodocyclopent-2-ene

: 953786-54-4
2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-N-methoxy-N-methylacetamide

: 953786-58-8
2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-((3R,5S)-5-tert-butyldimethylsilyloxy-3-(triethylsilyloxy)cyclopent-1-enyl)ethanone

Guidance literature:: (1S,4R)-1-(tert-butyldimethylsilyloxy)-4-(triethylsilyloxy)-2-iodocyclopent-2-ene; With TurboGrignard; 15-crown-5; In tetrahydrofuran; at -20 - 20 ℃;

2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-N-methoxy-N-methylacetamide; In tetrahydrofuran; at -20 - 0 ℃; for 7h; Further stages.;
DOI:10.1021/ol701757f

Reference yield:

: 909766-98-9
4-benzyloxy-6-iodo-2,3-dimethoxybenzaldehyde

: 953786-58-8
2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-((3R,5S)-5-tert-butyldimethylsilyloxy-3-(triethylsilyloxy)cyclopent-1-enyl)ethanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: KOt-Bu / tetrahydrofuran / 0 - 20 °C

1.2: tetrahydrofuran / 16 h / 20 °C

2.1: 423 mg / aq. HCl / acetone / 12 h / Heating

3.1: 2-methyl-2-butene; NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 20 °C

4.1: triethylamine; pivaloyl chloride / CH₂Cl₂ / 0 °C

4.2: 31.8 mg / triethylamine / CH₂Cl₂ / 2 h / 0 °C

5.1: i-PrMgCl*LiCl; 15-crown-5 / tetrahydrofuran / -20 - 20 °C

5.2: 63 percent / tetrahydrofuran / 7 h / -20 - 0 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; TurboGrignard; 2-methyl-but-2-ene; 15-crown-5; potassium tert-butylate; pivaloyl chloride; triethylamine; In tetrahydrofuran; dichloromethane; water; acetone; tert-butyl alcohol; 1.2: Wittig reaction;
DOI:10.1021/ol701757f

Reference yield:

: 953786-52-2
2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)acetaldehyde

: 953786-58-8
2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-((3R,5S)-5-tert-butyldimethylsilyloxy-3-(triethylsilyloxy)cyclopent-1-enyl)ethanone

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2-methyl-2-butene; NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 20 °C

2.1: triethylamine; pivaloyl chloride / CH₂Cl₂ / 0 °C

2.2: 31.8 mg / triethylamine / CH₂Cl₂ / 2 h / 0 °C

3.1: i-PrMgCl*LiCl; 15-crown-5 / tetrahydrofuran / -20 - 20 °C

3.2: 63 percent / tetrahydrofuran / 7 h / -20 - 0 °C

With sodium chlorite; sodium dihydrogenphosphate; TurboGrignard; 2-methyl-but-2-ene; 15-crown-5; pivaloyl chloride; triethylamine; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ol701757f