Methyl 11(R)-<(tert-butyldiphenylsilyl)oxy>-8-diazo-9-oxo-(Z,E,E)-5,12,14-eicosatrienoate

Base Information

Chemical Name:Methyl 11(R)-<(tert-butyldiphenylsilyl)oxy>-8-diazo-9-oxo-(Z,E,E)-5,12,14-eicosatrienoate
CAS No.:137696-41-4
Molecular Formula:C₃₇H₅₀N₂O₄Si
Molecular Weight:614.901
Hs Code.:

Synonyms:

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Chemical Property of Methyl 11(R)-<(tert-butyldiphenylsilyl)oxy>-8-diazo-9-oxo-(Z,E,E)-5,12,14-eicosatrienoate

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Technology Process of Methyl 11(R)-<(tert-butyldiphenylsilyl)oxy>-8-diazo-9-oxo-(Z,E,E)-5,12,14-eicosatrienoate

There total 16 articles about Methyl 11(R)-<(tert-butyldiphenylsilyl)oxy>-8-diazo-9-oxo-(Z,E,E)-5,12,14-eicosatrienoate 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:

: 28425-38-9
7-Chloro-3-heptyn-1-ol

: 137696-41-4
Methyl 11(R)-<(tert-butyldiphenylsilyl)oxy>-8-diazo-9-oxo-(Z,E,E)-5,12,14-eicosatrienoate

Guidance literature:: Multi-step reaction with 11 steps

1: 81 percent / NaI / dimethylformamide / 3 h / 100 °C

2: 98 percent / H₂, quinoline / Pd/BaSO₄ / ethyl acetate

3: 11.9 g / KOH / ethanol; H₂O / 12 h / 90 °C

4: 87 percent / BF₃*Et₂O / 5 h / 60 °C

5: 14.2 g / NEt₃ / diethyl ether / 1) 0 deg C, 1 h, 2) r.t., 2 h

6: 12.6 g / sodium azide / dimethylformamide / 6 h / 65 °C

7: 1) triphenylphosphine, 2) water / 1) ether, 0 deg C, 1 h, 2) r.t., 14 h

8: 89 percent / NEt₃ / tetrahydrofuran; diethyl ether / 2 h

9: 76 percent / NaOAc, NOx (from NaNO₂, conc. H₂SO₄) / CCl₄ / 1.5 h

10: 50percent ethereal KOH / methanol; diethyl ether / 0.5 h / 0 °C

11: diethyl ether; petroleum ether / 18 h / 4 °C

With quinoline; potassium hydroxide; sodium azide; NOx (from NaNO₂, conc. H₂SO₄); boron trifluoride diethyl etherate; water; hydrogen; sodium acetate; triethylamine; triphenylphosphine; sodium iodide; Pd-BaSO₄; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; Petroleum ether;
DOI:10.1021/jo00028a012

Reference yield:

: 86982-54-9
7-Hydroxy-4-heptynenitrile

: 137696-41-4
Methyl 11(R)-<(tert-butyldiphenylsilyl)oxy>-8-diazo-9-oxo-(Z,E,E)-5,12,14-eicosatrienoate

Guidance literature:: Multi-step reaction with 10 steps

1: 98 percent / H₂, quinoline / Pd/BaSO₄ / ethyl acetate

2: 11.9 g / KOH / ethanol; H₂O / 12 h / 90 °C

3: 87 percent / BF₃*Et₂O / 5 h / 60 °C

4: 14.2 g / NEt₃ / diethyl ether / 1) 0 deg C, 1 h, 2) r.t., 2 h

5: 12.6 g / sodium azide / dimethylformamide / 6 h / 65 °C

6: 1) triphenylphosphine, 2) water / 1) ether, 0 deg C, 1 h, 2) r.t., 14 h

7: 89 percent / NEt₃ / tetrahydrofuran; diethyl ether / 2 h

8: 76 percent / NaOAc, NOx (from NaNO₂, conc. H₂SO₄) / CCl₄ / 1.5 h

9: 50percent ethereal KOH / methanol; diethyl ether / 0.5 h / 0 °C

10: diethyl ether; petroleum ether / 18 h / 4 °C

With quinoline; potassium hydroxide; sodium azide; NOx (from NaNO₂, conc. H₂SO₄); boron trifluoride diethyl etherate; water; hydrogen; sodium acetate; triethylamine; triphenylphosphine; Pd-BaSO₄; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; Petroleum ether;
DOI:10.1021/jo00028a012

Reference yield:

: 25152-84-5,65909-91-3
trans,trans-2,4-decadienal

: 137696-41-4
Methyl 11(R)-<(tert-butyldiphenylsilyl)oxy>-8-diazo-9-oxo-(Z,E,E)-5,12,14-eicosatrienoate

Guidance literature:: Multi-step reaction with 5 steps

1: TiCl₄ / CH₂Cl₂ / 3 h / -78 °C

2: 71 percent / LiOH*H₂O / 1,2-dimethoxy-ethane; H₂O / 14 h / 60 °C

3: 1) imidazole, 4-(dimethylamino)pyridine, 2) water / 1) CH₂Cl₂, 0 deg C, 3 h, 2) 1 h

4: NEt₃ / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

5: diethyl ether; petroleum ether / 18 h / 4 °C

With 1H-imidazole; dmap; lithium hydroxide; water; titanium tetrachloride; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; Petroleum ether;
DOI:10.1021/jo00028a012