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

Base Information

Chemical Name:(1R,4S)-3-((S)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-chloroethyl)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enol
CAS No.:953786-65-7
Molecular Formula:C₂₈H₃₈ClIO₅Si
Molecular Weight:645.05
Hs Code.:

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

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

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

There total 15 articles about (1R,4S)-3-((S)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-chloroethyl)-4-(tert-butyldimethylsilyloxy)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: 72.0%

: 953786-60-2
(S)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-((3R,5S)-5-tert-butyldimethylsilyloxy-3-(triethylsilyloxy)cyclopent-1-enyl)-1-chloroethane

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

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1021/ol701757f

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 8 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

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; TurboGrignard; borane-THF; 2-methyl-but-2-ene; 15-crown-5; potassium tert-butylate; pivaloyl chloride; pyridine hydrogenfluoride; methanesulfonyl 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

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

Guidance literature:: Multi-step reaction with 9 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

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