(2S,5R,7S,8R)-2-Benzyloxymethyl-7-(4-methoxy-benzyloxy)-5-methyl-8-triisopropylsilanyloxymethyl-oxocan-3-one

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Chemical Name:(2S,5R,7S,8R)-2-Benzyloxymethyl-7-(4-methoxy-benzyloxy)-5-methyl-8-triisopropylsilanyloxymethyl-oxocan-3-one
CAS No.:865540-42-7
Molecular Formula:C₃₄H₅₂O₆Si
Molecular Weight:584.869
Hs Code.:

Synonyms:(2S,5R,7S,8R)-2-Benzyloxymethyl-7-(4-methoxy-benzyloxy)-5-methyl-8-triisopropylsilanyloxymethyl-oxocan-3-one

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Chemical Property of (2S,5R,7S,8R)-2-Benzyloxymethyl-7-(4-methoxy-benzyloxy)-5-methyl-8-triisopropylsilanyloxymethyl-oxocan-3-one

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Technology Process of (2S,5R,7S,8R)-2-Benzyloxymethyl-7-(4-methoxy-benzyloxy)-5-methyl-8-triisopropylsilanyloxymethyl-oxocan-3-one

There total 19 articles about (2S,5R,7S,8R)-2-Benzyloxymethyl-7-(4-methoxy-benzyloxy)-5-methyl-8-triisopropylsilanyloxymethyl-oxocan-3-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: 89.0%

: 865540-20-1
(2S,3R,5S,7S,8R)-2-Benzyloxymethyl-7-(4-methoxy-benzyloxy)-5-methyl-8-triisopropylsilanyloxymethyl-oxocan-3-ol

: 865540-42-7
(2S,5R,7S,8R)-2-Benzyloxymethyl-7-(4-methoxy-benzyloxy)-5-methyl-8-triisopropylsilanyloxymethyl-oxocan-3-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1021/ol051543m

Reference yield:

: 865540-36-9
(2R,3S)-2-Allyloxy-5-methyl-hex-5-ene-1,3-diol

: 865540-42-7
(2S,5R,7S,8R)-2-Benzyloxymethyl-7-(4-methoxy-benzyloxy)-5-methyl-8-triisopropylsilanyloxymethyl-oxocan-3-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: 95 percent / imidazole / dimethylformamide / 15 h / 20 °C

2.1: 86 percent / sodium hydride / dimethylformamide; various solvent(s) / 0 - 20 °C

3.1: 86 percent / Ti(Oi-Pr)4; n-BuMgCl / diethyl ether / 0 °C

4.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.17 h / 0 °C

4.2: 91 percent / tetrahydrofuran; various solvent(s); dimethylformamide / 0 - 20 °C

5.1: triethylamine / tetrahydrofuran / -78 - 0 °C

6.1: 90 percent / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

7.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.75 h / -78 °C

7.2: 93 percent / tetrahydrofuran; toluene / 0.5 h / -78 °C

8.1: 81 percent / lithium borohydride / diethyl ether; methanol; tetrahydrofuran / 1 h / 0 °C

9.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

10.1: 80 percent / tetrahydrofuran / 0.08 h / 0 °C

11.1: [Cl₂(PCy₃)(sIMes)Ru=CHPh] / CH₂Cl₂ / 12 h / Heating

12.1: 93 percent / hydrogen / [PCy₃][COD][Pyr]Ir⁽¹⁺⁾*PF₆^(1-) / CH₂Cl₂ / 2 h / -50 °C

13.1: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; lithium borohydride; n-butyllithium; oxalyl dichloride; hydrogen; butyl magnesium bromide; sodium hexamethyldisilazane; sodium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; (η4-1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate; [Cl₂(PCy₃)(sIMes)Ru=CHPh]; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 9.1: Swern oxidation;
DOI:10.1021/ol051543m

Reference yield:

: 865540-38-1
(2R,3S)-3-(4-Methoxy-benzyloxy)-5-methyl-1-triisopropylsilanyloxy-hex-5-en-2-ol

: 865540-42-7
(2S,5R,7S,8R)-2-Benzyloxymethyl-7-(4-methoxy-benzyloxy)-5-methyl-8-triisopropylsilanyloxymethyl-oxocan-3-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.17 h / 0 °C

1.2: 91 percent / tetrahydrofuran; various solvent(s); dimethylformamide / 0 - 20 °C

2.1: triethylamine / tetrahydrofuran / -78 - 0 °C

3.1: 90 percent / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

4.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.75 h / -78 °C

4.2: 93 percent / tetrahydrofuran; toluene / 0.5 h / -78 °C

5.1: 81 percent / lithium borohydride / diethyl ether; methanol; tetrahydrofuran / 1 h / 0 °C

6.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

7.1: 80 percent / tetrahydrofuran / 0.08 h / 0 °C

8.1: [Cl₂(PCy₃)(sIMes)Ru=CHPh] / CH₂Cl₂ / 12 h / Heating

9.1: 93 percent / hydrogen / [PCy₃][COD][Pyr]Ir⁽¹⁺⁾*PF₆^(1-) / CH₂Cl₂ / 2 h / -50 °C

10.1: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With lithium borohydride; n-butyllithium; oxalyl dichloride; hydrogen; sodium hexamethyldisilazane; sodium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; (η4-1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate; [Cl₂(PCy₃)(sIMes)Ru=CHPh]; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; 6.1: Swern oxidation;
DOI:10.1021/ol051543m