(8-benzyloxy-4-hydroxy-6-methyl-2-oxo-oct-6-enyl)-phosphonic acid dimethyl ester

Base Information

Chemical Name:(8-benzyloxy-4-hydroxy-6-methyl-2-oxo-oct-6-enyl)-phosphonic acid dimethyl ester
CAS No.:916757-43-2
Molecular Formula:C₁₈H₂₇O₆P
Molecular Weight:370.383
Hs Code.:

Synonyms:(8-benzyloxy-4-hydroxy-6-methyl-2-oxo-oct-6-enyl)-phosphonic acid dimethyl ester

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Chemical Property of (8-benzyloxy-4-hydroxy-6-methyl-2-oxo-oct-6-enyl)-phosphonic acid dimethyl ester

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Technology Process of (8-benzyloxy-4-hydroxy-6-methyl-2-oxo-oct-6-enyl)-phosphonic acid dimethyl ester

There total 12 articles about (8-benzyloxy-4-hydroxy-6-methyl-2-oxo-oct-6-enyl)-phosphonic acid dimethyl 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: 92.0%

: 916757-50-1
[8-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-oxo-oct-6-enyl]-phosphonic acid dimethyl ester

: 916757-43-2
(8-benzyloxy-4-hydroxy-6-methyl-2-oxo-oct-6-enyl)-phosphonic acid dimethyl ester

Guidance literature:: With hydrogen fluoride; In acetonitrile; at 25 ℃; for 3h;
DOI:10.1002/anie.200601867 DOI:10.1021/ja068053p

Reference yield:

: 916757-46-5
5,7-bis-(tert-butyl-dimethyl-silanyloxy)-hept-2-yn-1-ol

: 916757-43-2
(8-benzyloxy-4-hydroxy-6-methyl-2-oxo-oct-6-enyl)-phosphonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: Red-Al / tetrahydrofuran; toluene / 0.75 h / 25 °C

1.2: 66 percent / N-iodosuccinimide / tetrahydrofuran; toluene / 0.5 h / -78 °C

2.1: triethylamine / tetrahydrofuran / 2 h / 25 °C

3.1: Pd(bis-(diphenylphosphino)ferrocene)Cl₂ / tetrahydrofuran; toluene / 12 h / 65 °C

4.1: 19.2 g / K₂CO₃ / methanol / 4 h / 25 °C

5.1: 88 percent / NaH; n-Bu₄NI / tetrahydrofuran / 6 h / 25 °C

6.1: 9 percent / HF*Py / tetrahydrofuran / 3 h / 0 °C

7.1: 73 percent / NaHCO₃; pyridinium chlorochromate / CH₂Cl₂ / 3 h / 25 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

8.2: tetrahydrofuran; hexane / 2 h / -78 °C

9.1: 11.1 g / pyridinium dichromate / dimethylformamide / 12 h / 25 °C

10.1: 92 percent / aq. HF / acetonitrile / 3 h / 25 °C

With dipyridinium dichromate; n-butyllithium; hydrogen fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; pyridine hydrogenfluoride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: Negishi coupling;
DOI:10.1021/ja068053p

Reference yield:

: 5,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-iodo-1-trimethylsilanyloxy-hept-2-ene

: 916757-43-2
(8-benzyloxy-4-hydroxy-6-methyl-2-oxo-oct-6-enyl)-phosphonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: Pd(bis-(diphenylphosphino)ferrocene)Cl₂ / tetrahydrofuran; toluene / 12 h / 65 °C

2: 19.2 g / K₂CO₃ / methanol / 4 h / 25 °C

3: 88 percent / NaH; n-Bu₄NI / tetrahydrofuran / 6 h / 25 °C

4: 9 percent / HF*Py / tetrahydrofuran / 3 h / 0 °C

5: 73 percent / NaHCO₃; pyridinium chlorochromate / CH₂Cl₂ / 3 h / 25 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; pyridine hydrogenfluoride; pyridinium chlorochromate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: Negishi coupling;
DOI:10.1021/ja068053p