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

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Chemical Name:(R)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-((3R,5S)-5-tert-butyldimethylsilyloxy-3-(triethylsilyloxy)cyclopent-1-enyl)ethanol
CAS No.:953786-59-9
Molecular Formula:C₃₄H₅₃IO₆Si₂
Molecular Weight:740.867
Hs Code.:

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

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

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

There total 15 articles about (R)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-((3R,5S)-5-tert-butyldimethylsilyloxy-3-(triethylsilyloxy)cyclopent-1-enyl)ethanol 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:

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

: 953786-59-9
(R)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-((3R,5S)-5-tert-butyldimethylsilyloxy-3-(triethylsilyloxy)cyclopent-1-enyl)ethanol

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

Guidance literature:: With borane-THF; (R)-Corey-Bakshi-Shibata catalyst; In tetrahydrofuran; at 10 ℃; for 3h;
DOI:10.1021/ol701757f

Reference yield:

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

: 953786-59-9
(R)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-((3R,5S)-5-tert-butyldimethylsilyloxy-3-(triethylsilyloxy)cyclopent-1-enyl)ethanol

Guidance literature:: Multi-step reaction with 6 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

6.1: BH₃*THF complex / (R)-Corey-Bakshi-Shibata catalyst / tetrahydrofuran / 3 h / 10 °C

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

Reference yield:

: 953786-63-5
(1S,4R)-4-(triethylsilyloxy)cyclopent-2-enyl pivalate

: 953786-59-9
(R)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-((3R,5S)-5-tert-butyldimethylsilyloxy-3-(triethylsilyloxy)cyclopent-1-enyl)ethanol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 91 percent / DIBAL-H / toluene / 2 h / -78 °C

2.1: 87 percent / NaOAc; molecular sieves 4 Angstroem; pyridinium chlorochromate / CH₂Cl₂ / 0 - 20 °C

3.1: 82 percent / I₂; pyridine / CCl₄ / 0 - 20 °C

4.1: 72 percent / CeCl₃*7H₂O; NaBH₄ / methanol / -60 - 20 °C

5.1: 98 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

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

6.2: 63 percent / tetrahydrofuran / 7 h / -20 - 0 °C

7.1: BH₃*THF complex / (R)-Corey-Bakshi-Shibata catalyst / tetrahydrofuran / 3 h / 10 °C

With pyridine; dmap; sodium tetrahydroborate; TurboGrignard; cerium(III) chloride; borane-THF; 15-crown-5; 4 A molecular sieve; iodine; sodium acetate; diisobutylaluminium hydride; triethylamine; pyridinium chlorochromate; (R)-Corey-Bakshi-Shibata catalyst; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; toluene; 4.1: Luche reduction;
DOI:10.1021/ol701757f