methyl (2S)-2-{[tert-butyl(diphenyl)silyl]oxy}-6-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hex-4-ynoate

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Chemical Name:methyl (2S)-2-{[tert-butyl(diphenyl)silyl]oxy}-6-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hex-4-ynoate
CAS No.:302554-89-8
Molecular Formula:C₂₈H₃₆O₅Si
Molecular Weight:480.676
Hs Code.:

Synonyms:methyl (2S)-2-{[tert-butyl(diphenyl)silyl]oxy}-6-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hex-4-ynoate

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Chemical Property of methyl (2S)-2-{[tert-butyl(diphenyl)silyl]oxy}-6-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hex-4-ynoate

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Technology Process of methyl (2S)-2-{[tert-butyl(diphenyl)silyl]oxy}-6-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hex-4-ynoate

There total 7 articles about methyl (2S)-2-{[tert-butyl(diphenyl)silyl]oxy}-6-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hex-4-ynoate 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: 80.0%

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 2-(tert-butyl-diphenyl-silanyloxy)-6-(tetrahydro-pyran-2-yloxy)-hex-4-ynoic acid

: 302554-89-8
methyl (2S)-2-{[tert-butyl(diphenyl)silyl]oxy}-6-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hex-4-ynoate

Guidance literature:: In diethyl ether;
DOI:10.1016/S0040-4039(00)00961-8

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 302554-89-8
methyl (2S)-2-{[tert-butyl(diphenyl)silyl]oxy}-6-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hex-4-ynoate

Guidance literature:: Multi-step reaction with 7 steps

1: 81 percent / imidazole / dimethylformamide / 4 h / 20 °C

2: 91 percent / DIBALH / CH₂Cl₂; heptane / -78 - 20 °C

3: 78 percent / TsOH / 0.33 h / 20 °C

4: 97 percent / DDQ / CH₂Cl₂; H₂O / 1 h / 20 °C

5: SO₃*pyridine; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0.5 h / 0 °C

6: NaClO₂; aq. K₂HPO₄; 2,3-dimethylbut-2-ene / 2-methyl-propan-2-ol / 2 h / 0 °C

7: 1.71 g / diethyl ether

With 1H-imidazole; sodium chlorite; dipotassium hydrogenphosphate; 2,3-Dimethyl-2-butene; pyridine-SO₃ complex; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; n-heptane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; 6: Pinnick oxidation;
DOI:10.1021/jo026743f

Reference yield:

: 2-(tert-butyl-diphenyl-silanyloxy)-6-(tetrahydro-pyran-2-yloxy)-hex-4-ynal

: 302554-89-8
methyl (2S)-2-{[tert-butyl(diphenyl)silyl]oxy}-6-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hex-4-ynoate

Guidance literature:: Multi-step reaction with 2 steps

1: NaClO₂; aq. K₂HPO₄; 2,3-dimethylbut-2-ene / 2-methyl-propan-2-ol / 2 h / 0 °C

2: 1.71 g / diethyl ether

With sodium chlorite; dipotassium hydrogenphosphate; 2,3-Dimethyl-2-butene; In diethyl ether; tert-butyl alcohol; 1: Pinnick oxidation;
DOI:10.1021/jo026743f