(5S,6S)-6-((E)-2-{(2R,4R,5R)-5-allyl-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-[2-(trityloxy)ethyl]-[1,3]dioxolan-4-yl}vinyl)-5-ethyl-5,6-dihydro-2H-pyran-2-one

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Chemical Name:(5S,6S)-6-((E)-2-{(2R,4R,5R)-5-allyl-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-[2-(trityloxy)ethyl]-[1,3]dioxolan-4-yl}vinyl)-5-ethyl-5,6-dihydro-2H-pyran-2-one
CAS No.:521274-29-3
Molecular Formula:C₄₈H₅₆O₆Si
Molecular Weight:757.055
Hs Code.:

Synonyms:(5S,6S)-6-((E)-2-{(2R,4R,5R)-5-allyl-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-[2-(trityloxy)ethyl]-[1,3]dioxolan-4-yl}vinyl)-5-ethyl-5,6-dihydro-2H-pyran-2-one

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Chemical Property of (5S,6S)-6-((E)-2-{(2R,4R,5R)-5-allyl-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-[2-(trityloxy)ethyl]-[1,3]dioxolan-4-yl}vinyl)-5-ethyl-5,6-dihydro-2H-pyran-2-one

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MSDS Files:: SDS file from LookChem

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Technology Process of (5S,6S)-6-((E)-2-{(2R,4R,5R)-5-allyl-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-[2-(trityloxy)ethyl]-[1,3]dioxolan-4-yl}vinyl)-5-ethyl-5,6-dihydro-2H-pyran-2-one

There total 25 articles about (5S,6S)-6-((E)-2-{(2R,4R,5R)-5-allyl-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-[2-(trityloxy)ethyl]-[1,3]dioxolan-4-yl}vinyl)-5-ethyl-5,6-dihydro-2H-pyran-2-one 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: 99.0%

: 521274-28-2
ethyl (2Z,4S,5S,6E)-7-{(2R,4R,5R)-5-allyl-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-[2-(tritylioxy)ethyl]-[1,3]dioxolan-4-yl}-4-ethyl-5-hydroxyhepta-2,6-dienoate

: 521274-29-3
(5S,6S)-6-((E)-2-{(2R,4R,5R)-5-allyl-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-[2-(trityloxy)ethyl]-[1,3]dioxolan-4-yl}vinyl)-5-ethyl-5,6-dihydro-2H-pyran-2-one

Guidance literature:: With titanium(IV) isopropylate; In benzene; at 80 ℃; for 0.25h;
DOI:10.1021/ja0340679

Reference yield:

: 120743-99-9
p-[(tert-butyldimethylsilyl)oxy]benzaldehyde

: 521274-29-3
(5S,6S)-6-((E)-2-{(2R,4R,5R)-5-allyl-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-[2-(trityloxy)ethyl]-[1,3]dioxolan-4-yl}vinyl)-5-ethyl-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 12 steps

1.1: 6.82 g / CSA / methanol / 20 h / 23 °C

2.1: CSA / dimethylformamide / 0.67 h / 50 °C

3.1: 4.67 g / TBAF / tetrahydrofuran / 1.5 h / 20 °C

4.1: MnO₂ / CH₂Cl₂ / 3 h / 20 °C

5.1: 2.51 g / imidazole / CH₂Cl₂ / 1 h / 20 °C

6.1: n-Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 0.67 h / 0 °C

6.2: CH₂Cl₂ / 5 h / -78 - 20 °C

7.1: imidazole / dimethylformamide / 0.08 h / 20 °C

8.1: 1.02 g / tetrahydrofuran; hexane / 1.5 h / 0 °C

9.1: DIBAL / toluene / -78 °C

10.1: (n-Bu)4N⁽¹⁺⁾*OH^(1-) / tetrahydrofuran; methanol / 3.5 h / -78 - -18 °C

11.1: PPTS / methanol; tetrahydrofuran / 1 h / 20 °C

12.1: 99 percent / Ti(Oi-Pr)4 / benzene / 0.25 h / 80 °C

With 1H-imidazole; titanium(IV) isopropylate; manganese(IV) oxide; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/ja0340679

Reference yield:

: 123-08-0,65581-83-1
4-hydroxy-benzaldehyde

: 521274-29-3
(5S,6S)-6-((E)-2-{(2R,4R,5R)-5-allyl-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-[2-(trityloxy)ethyl]-[1,3]dioxolan-4-yl}vinyl)-5-ethyl-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: imidazole / CH₂Cl₂ / 0.5 h / 23 °C

2.1: 6.82 g / CSA / methanol / 20 h / 23 °C

3.1: CSA / dimethylformamide / 0.67 h / 50 °C

4.1: 4.67 g / TBAF / tetrahydrofuran / 1.5 h / 20 °C

5.1: MnO₂ / CH₂Cl₂ / 3 h / 20 °C

6.1: 2.51 g / imidazole / CH₂Cl₂ / 1 h / 20 °C

7.1: n-Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 0.67 h / 0 °C

7.2: CH₂Cl₂ / 5 h / -78 - 20 °C

8.1: imidazole / dimethylformamide / 0.08 h / 20 °C

9.1: 1.02 g / tetrahydrofuran; hexane / 1.5 h / 0 °C

10.1: DIBAL / toluene / -78 °C

11.1: (n-Bu)4N⁽¹⁺⁾*OH^(1-) / tetrahydrofuran; methanol / 3.5 h / -78 - -18 °C

12.1: PPTS / methanol; tetrahydrofuran / 1 h / 20 °C

13.1: 99 percent / Ti(Oi-Pr)4 / benzene / 0.25 h / 80 °C

With 1H-imidazole; titanium(IV) isopropylate; manganese(IV) oxide; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/ja0340679