(E)-(S)-8-Hydroxy-4,8-dimethyl-7-(toluene-4-sulfonyloxy)-non-3-enoic acid tert-butyl ester

Base Information

Chemical Name:(E)-(S)-8-Hydroxy-4,8-dimethyl-7-(toluene-4-sulfonyloxy)-non-3-enoic acid tert-butyl ester
CAS No.:771531-64-7
Molecular Formula:C₂₂H₃₄O₆S
Molecular Weight:426.574
Hs Code.:

Synonyms:(E)-(S)-8-Hydroxy-4,8-dimethyl-7-(toluene-4-sulfonyloxy)-non-3-enoic acid tert-butyl ester

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Chemical Property of (E)-(S)-8-Hydroxy-4,8-dimethyl-7-(toluene-4-sulfonyloxy)-non-3-enoic acid tert-butyl ester

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Technology Process of (E)-(S)-8-Hydroxy-4,8-dimethyl-7-(toluene-4-sulfonyloxy)-non-3-enoic acid tert-butyl ester

There total 5 articles about (E)-(S)-8-Hydroxy-4,8-dimethyl-7-(toluene-4-sulfonyloxy)-non-3-enoic acid tert-butyl 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: 86.0%

: 771531-63-6
(E)-(S)-7,8-Dihydroxy-4,8-dimethyl-non-3-enoic acid tert-butyl ester

: 4124-41-8
p-toluenesulfonylanhydride

: 771531-64-7
(E)-(S)-8-Hydroxy-4,8-dimethyl-7-(toluene-4-sulfonyloxy)-non-3-enoic acid tert-butyl ester

Guidance literature:: With pyridine; at 0 ℃; for 1h;
DOI:10.1002/chem.200400407

Reference yield:

: 21677-96-3
geranyl cyanide

: 771531-64-7
(E)-(S)-8-Hydroxy-4,8-dimethyl-7-(toluene-4-sulfonyloxy)-non-3-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

1.2: aq. HCl; NH₄Cl / ethyl acetate; CH₂Cl₂ / 0.33 h / 20 °C

2.1: 2.9 g / Jones reagent / acetone / -20 °C

3.1: 95 percent / aq. (TFA)2O / 0.25 h / 25 °C

4.1: 61 percent / aq. K₃Fe(CN)6; K₂CO₃; hydroquinine 1,4-phthalazinediyl diether / K₂OsO₂(OH)4; CH₃SO₂NH₂ / 2-methyl-propan-2-ol / 12 h / 0 °C

5.1: 86 percent / pyridine / 1 h / 0 °C

With pyridine; jones reagent; Hydroquinone 1,4-phthalazinediyl diether; diisobutylaluminium hydride; potassium carbonate; trifluoroacetic anhydride; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; In dichloromethane; acetone; tert-butyl alcohol; 4.1: Sharpless asymmetric dihydroxylation;
DOI:10.1002/chem.200400407

Reference yield:

: 459-85-8
(E)-4,8-dimethylnona-3,7-dienoic acid

: 771531-64-7
(E)-(S)-8-Hydroxy-4,8-dimethyl-7-(toluene-4-sulfonyloxy)-non-3-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / aq. (TFA)2O / 0.25 h / 25 °C

2: 61 percent / aq. K₃Fe(CN)6; K₂CO₃; hydroquinine 1,4-phthalazinediyl diether / K₂OsO₂(OH)4; CH₃SO₂NH₂ / 2-methyl-propan-2-ol / 12 h / 0 °C

3: 86 percent / pyridine / 1 h / 0 °C

With pyridine; Hydroquinone 1,4-phthalazinediyl diether; potassium carbonate; trifluoroacetic anhydride; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; In tert-butyl alcohol; 2: Sharpless asymmetric dihydroxylation;
DOI:10.1002/chem.200400407