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

Base Information

Chemical Name:(S)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-((3R,5S)-5-tert-butyldimethylsilyloxy-3-(triethylsilyloxy)cyclopent-1-enyl)-1-chloroethane
CAS No.:953786-60-2
Molecular Formula:C₃₄H₅₂ClIO₅Si₂
Molecular Weight:759.312
Hs Code.:

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

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

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

There total 16 articles about (S)-2-(4-(benzyloxy)-6-iodo-2,3-dimethoxyphenyl)-1-((3R,5S)-5-tert-butyldimethylsilyloxy-3-(triethylsilyloxy)cyclopent-1-enyl)-1-chloroethane 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: 65.0%

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

: 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

Guidance literature:: With methanesulfonyl chloride; triethylamine; In dichloromethane; at -25 - 0 ℃;
DOI:10.1021/ol701757f

Reference yield: 65.0%

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

: 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

Guidance literature:: With methanesulfonyl chloride; triethylamine; In dichloromethane; at -25 - 0 ℃; Inert atmosphere;
DOI:10.1021/jo902006q

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 7 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

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