[(2R,4R,6S)-6-((Z)-(R)-7-Benzyloxy-4-hydroxy-2-oxo-6-triethylsilanyloxy-hept-3-enyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester

Base Information

Chemical Name:[(2R,4R,6S)-6-((Z)-(R)-7-Benzyloxy-4-hydroxy-2-oxo-6-triethylsilanyloxy-hept-3-enyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester
CAS No.:625124-66-5
Molecular Formula:C₃₇H₅₄O₉Si
Molecular Weight:670.916
Hs Code.:

Synonyms:[(2R,4R,6S)-6-((Z)-(R)-7-Benzyloxy-4-hydroxy-2-oxo-6-triethylsilanyloxy-hept-3-enyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester

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Chemical Property of [(2R,4R,6S)-6-((Z)-(R)-7-Benzyloxy-4-hydroxy-2-oxo-6-triethylsilanyloxy-hept-3-enyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester

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Technology Process of [(2R,4R,6S)-6-((Z)-(R)-7-Benzyloxy-4-hydroxy-2-oxo-6-triethylsilanyloxy-hept-3-enyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester

There total 13 articles about [(2R,4R,6S)-6-((Z)-(R)-7-Benzyloxy-4-hydroxy-2-oxo-6-triethylsilanyloxy-hept-3-enyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester 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:

: 625124-80-3
[(2R,4R,6S)-6-((2RS,6R)-7-benzyloxy-2-hydroxy-4-oxo-6-triethylsilanyloxyheptyl)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]acetic acid tert-butyl ester

: 625124-66-5
[(2R,4R,6S)-6-((Z)-(R)-7-Benzyloxy-4-hydroxy-2-oxo-6-triethylsilanyloxy-hept-3-enyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester

Guidance literature:: With Dess-Martin periodane; In tetrahydrofuran; dichloromethane; water; for 24h;
DOI:10.1021/ja030316h

Reference yield:

: 540-88-5
acetic acid tert-butyl ester

: 625124-66-5
[(2R,4R,6S)-6-((Z)-(R)-7-Benzyloxy-4-hydroxy-2-oxo-6-triethylsilanyloxy-hept-3-enyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: LDA / tetrahydrofuran; hexane / 1 h

1.2: tetrahydrofuran; hexane / 0.5 h / Heating

2.1: 87.3 g / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol

3.1: PPTS / CH₂Cl₂ / 2.5 h / Heating

4.1: 33.0 g / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 1 h

5.1: Et₃N / CH₂Cl₂ / 4.25 h / 20 °C

6.1: NaI; NaHCO₃; Na₂SO₃ / butan-2-one / 16 h / Heating

7.1: Li₂CuCl₄ / tetrahydrofuran

8.1: O₃ / CH₂Cl₂; methanol / 1 h

8.2: 33.6 g / tributylphosphine / CH₂Cl₂; methanol / 0.17 h

9.1: LDA / tetrahydrofuran; hexane / 1 h

9.2: 50.8 g / tetrahydrofuran; hexane / 0.25 h

10.1: Dess-Martin periodinane / H₂O; tetrahydrofuran; CH₂Cl₂ / 24 h

With sodium tetrahydroborate; dilithium tetrachlorocuprate; diethyl methoxy borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; ozone; triethylamine; sodium iodide; sodium sulfite; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; butanone; 1.2: Claisen condensation / 10.1: Dess-Martin oxidation;
DOI:10.1021/ja030316h

Reference yield:

: 604775-07-7
(2R)-1-(benzyloxy)-4-methyl-4-penten-2-ol

: 625124-66-5
[(2R,4R,6S)-6-((Z)-(R)-7-Benzyloxy-4-hydroxy-2-oxo-6-triethylsilanyloxy-hept-3-enyl)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: imidazole / dimethylformamide / 0 - 20 °C

2.1: O₃; NaHCO₃ / methanol; CH₂Cl₂

2.2: 51.1 g / dimethyl sulfide / methanol; CH₂Cl₂ / 12 h

3.1: LDA / tetrahydrofuran; hexane / 1 h

3.2: 50.8 g / tetrahydrofuran; hexane / 0.25 h

4.1: Dess-Martin periodinane / H₂O; tetrahydrofuran; CH₂Cl₂ / 24 h

With 1H-imidazole; sodium hydrogencarbonate; Dess-Martin periodane; ozone; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; 4.1: Dess-Martin oxidation;
DOI:10.1021/ja030316h