Acrylic acid (E)-(1R,3S)-1-allyl-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-7-oxo-9-phenyl-non-8-enyl ester

Base Information

Chemical Name:Acrylic acid (E)-(1R,3S)-1-allyl-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-7-oxo-9-phenyl-non-8-enyl ester
CAS No.:885322-74-7
Molecular Formula:C₃₇H₄₄O₅Si
Molecular Weight:596.839
Hs Code.:

Synonyms:Acrylic acid (E)-(1R,3S)-1-allyl-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-7-oxo-9-phenyl-non-8-enyl ester

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Chemical Property of Acrylic acid (E)-(1R,3S)-1-allyl-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-7-oxo-9-phenyl-non-8-enyl ester

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Technology Process of Acrylic acid (E)-(1R,3S)-1-allyl-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-7-oxo-9-phenyl-non-8-enyl ester

There total 7 articles about Acrylic acid (E)-(1R,3S)-1-allyl-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-7-oxo-9-phenyl-non-8-enyl 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:

: 885322-69-0
(3S)-3-[(tert-butyldiphenylsilyl)oxy]-5-[(tert-butyldimethylsilyl)oxy]hexanal

: 885322-74-7
Acrylic acid (E)-(1R,3S)-1-allyl-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-7-oxo-9-phenyl-non-8-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: (+)-Ipc₂BOMe / diethyl ether / 0 - 20 °C

1.2: diethyl ether / 4 h / -100 °C

1.3: NaOH; H₂O₂ / diethyl ether; H₂O / 20 °C

2.1: 94 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

3.1: 89 percent / TsOH*2H₂O / tetrahydrofuran; H₂O / 7 h / 20 °C

4.1: 88 percent / Et₃N; oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

5.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C

5.2: 63 percent / tetrahydrofuran; hexane / 0.75 h / -78 °C

With oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; (+)-B-methoxydiisocamphenylborane; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; 1.2: Brown asymmetric alkylation / 4.1: Swern oxidation;
DOI:10.1021/jo060028e

Reference yield:

: 885322-68-9
(3R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]hex-5-ene

: 885322-74-7
Acrylic acid (E)-(1R,3S)-1-allyl-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-7-oxo-9-phenyl-non-8-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: N-methylmorpholine N-oxide; OsO₄ / tetrahydrofuran; H₂O / 10 h / 20 °C

1.2: 84 percent / NaIO₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

2.1: (+)-Ipc₂BOMe / diethyl ether / 0 - 20 °C

2.2: diethyl ether / 4 h / -100 °C

2.3: NaOH; H₂O₂ / diethyl ether; H₂O / 20 °C

3.1: 94 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

4.1: 89 percent / TsOH*2H₂O / tetrahydrofuran; H₂O / 7 h / 20 °C

5.1: 88 percent / Et₃N; oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

6.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C

6.2: 63 percent / tetrahydrofuran; hexane / 0.75 h / -78 °C

With osmium(VIII) oxide; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; (+)-B-methoxydiisocamphenylborane; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; 2.2: Brown asymmetric alkylation / 5.1: Swern oxidation;
DOI:10.1021/jo060028e

Reference yield:

: 885322-72-5
(1R)-1-{(2S)-2-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-4-hydroxybutyl}-3-butenyl acrylate

: 885322-74-7
Acrylic acid (E)-(1R,3S)-1-allyl-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-7-oxo-9-phenyl-non-8-enyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 88 percent / Et₃N; oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

2.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C

2.2: 63 percent / tetrahydrofuran; hexane / 0.75 h / -78 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 1.1: Swern oxidation;
DOI:10.1021/jo060028e