(S)-3-((S)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-chloroethyl)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enone

Base Information

Chemical Name:(S)-3-((S)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-chloroethyl)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enone
CAS No.:953786-50-0
Molecular Formula:C₂₈H₃₆ClIO₅Si
Molecular Weight:643.034
Hs Code.:

Synonyms:(S)-3-((S)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-chloroethyl)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enone

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Chemical Property of (S)-3-((S)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-chloroethyl)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enone

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Technology Process of (S)-3-((S)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-chloroethyl)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enone

There total 16 articles about (S)-3-((S)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-chloroethyl)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enone 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: 88.0%

: 953786-65-7
(1R,4S)-3-((S)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-chloroethyl)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enol

: 953786-50-0
(S)-3-((S)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-chloroethyl)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enone

Guidance literature:: With 4 A molecular sieve; sodium acetate; pyridinium chlorochromate; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ol701757f

Reference yield:

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

: 953786-50-0
(S)-3-((S)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-chloroethyl)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enone

Guidance literature:: Multi-step reaction with 9 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

7.1: 65 percent / triethylamine; methanesulfonyl chloride / CH₂Cl₂ / -25 - 0 °C

8.1: 72 percent / HF*pyridine complex / tetrahydrofuran / 0 - 20 °C

9.1: 88 percent / NaOAc; molecular sieves 4 Angstroem; pyridinium chlorochromate / CH₂Cl₂ / 0 - 20 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; TurboGrignard; borane-THF; 2-methyl-but-2-ene; 15-crown-5; 4 A molecular sieve; potassium tert-butylate; sodium acetate; pivaloyl chloride; pyridine hydrogenfluoride; methanesulfonyl chloride; triethylamine; pyridinium chlorochromate; (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

: 953786-50-0
(S)-3-((S)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-chloroethyl)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enone

Guidance literature:: Multi-step reaction with 10 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

8.1: 65 percent / triethylamine; methanesulfonyl chloride / CH₂Cl₂ / -25 - 0 °C

9.1: 72 percent / HF*pyridine complex / tetrahydrofuran / 0 - 20 °C

10.1: 88 percent / NaOAc; molecular sieves 4 Angstroem; pyridinium chlorochromate / CH₂Cl₂ / 0 - 20 °C

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