(2S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-6-[(4-methoxybenzyl)oxy]-3-(phenylsulfonyl)-2,5,5-trimethyloct-7-en-4-one

Base Information

Chemical Name:(2S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-6-[(4-methoxybenzyl)oxy]-3-(phenylsulfonyl)-2,5,5-trimethyloct-7-en-4-one
CAS No.:366454-95-7
Molecular Formula:C₄₁H₅₀O₆SSi
Molecular Weight:698.996
Hs Code.:

Synonyms:(2S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-6-[(4-methoxybenzyl)oxy]-3-(phenylsulfonyl)-2,5,5-trimethyloct-7-en-4-one

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Chemical Property of (2S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-6-[(4-methoxybenzyl)oxy]-3-(phenylsulfonyl)-2,5,5-trimethyloct-7-en-4-one

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Technology Process of (2S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-6-[(4-methoxybenzyl)oxy]-3-(phenylsulfonyl)-2,5,5-trimethyloct-7-en-4-one

There total 14 articles about (2S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-6-[(4-methoxybenzyl)oxy]-3-(phenylsulfonyl)-2,5,5-trimethyloct-7-en-4-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:

: 366454-93-5
(2S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-6-[(4-methoxybenzyl)oxy]-3-(phenylsulfonyl)-2,5,5-trimethyl-oct-7-en-4-ol

: 366454-95-7
(2S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-6-[(4-methoxybenzyl)oxy]-3-(phenylsulfonyl)-2,5,5-trimethyloct-7-en-4-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/jo0503862

Reference yield:

: 366454-86-6
(2S,4S)-4-hydroxymethyl-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxane

: 366454-95-7
(2S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-6-[(4-methoxybenzyl)oxy]-3-(phenylsulfonyl)-2,5,5-trimethyloct-7-en-4-one

Guidance literature:: Multi-step reaction with 6 steps

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

2.1: n-BuLi / tetrahydrofuran; hexane / 0.67 h / 0 °C

2.2: tetrahydrofuran; hexane / 4 h / 0 °C

3.1: DIBAL-H / CH₂Cl₂ / -78 - 20 °C

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

5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

5.2: tetrahydrofuran; hexane / 1 h / -50 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With n-butyllithium; oxalyl dichloride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Swern oxidation / 2.2: Wittig methylenation / 4.1: Swern oxidation;
DOI:10.1021/jo0503862

Reference yield:

: 366454-87-7
(2S,4S)-5,5-dimethyl-2-(4-methoxyphenyl)-1,3-dioxan-4-carboxaldehyde

: 366454-95-7
(2S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-6-[(4-methoxybenzyl)oxy]-3-(phenylsulfonyl)-2,5,5-trimethyloct-7-en-4-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.67 h / 0 °C

1.2: tetrahydrofuran; hexane / 4 h / 0 °C

2.1: DIBAL-H / CH₂Cl₂ / -78 - 20 °C

3.1: oxalyl chloride DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

4.2: tetrahydrofuran; hexane / 1 h / -50 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With n-butyllithium; oxalyl dichloride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.2: Wittig methylenation / 3.1: Swern oxidation;
DOI:10.1021/jo0503862