tert-butyl (2-((2R,3S,6S)-6-(iodomethyl)-3-methyltetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane

Base Information

Chemical Name:tert-butyl (2-((2R,3S,6S)-6-(iodomethyl)-3-methyltetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane
CAS No.:623566-49-4
Molecular Formula:C₂₅H₃₅IO₂Si
Molecular Weight:522.542
Hs Code.:

Synonyms:tert-butyl (2-((2R,3S,6S)-6-(iodomethyl)-3-methyltetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane

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Chemical Property of tert-butyl (2-((2R,3S,6S)-6-(iodomethyl)-3-methyltetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane

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Technology Process of tert-butyl (2-((2R,3S,6S)-6-(iodomethyl)-3-methyltetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane

There total 6 articles about tert-butyl (2-((2R,3S,6S)-6-(iodomethyl)-3-methyltetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane 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: 87.0%

: 623566-59-6
((2S,5S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyltetrahydro-2H-pyran-2-yl)methanol

: 623566-49-4
tert-butyl (2-((2R,3S,6S)-6-(iodomethyl)-3-methyltetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane

Guidance literature:: With 2,6-dimethylpyridine; methyltriphenoxyphosphonium iodide; In N,N-dimethyl-formamide; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1021/jo802269q

Reference yield:

: methyl (2R,3S)-(E)-3-(dimethyl(phenyl)silyl)-2-(trimethylsilyloxy)-hex-4-enoate

: 623566-49-4
tert-butyl (2-((2R,3S,6S)-6-(iodomethyl)-3-methyltetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / TMSOTf / CH₂Cl₂ / 4 h / -50 °C

2: 99 percent / H₂ / Pd/C / ethyl acetate / 18 h / 20 °C / 760 Torr

3: 76 percent / aq. CH₃CO₃H; Hg(OAc)2 / 1 h / 20 °C

4: 99 percent / imidazole / dimethylformamide / 12 h / 0 - 20 °C

5: 90 percent / Dibal-H / CH₂Cl₂; hexane / 2.5 h / 0 °C

6: 86 percent / (PhO)3P⁺CH₃I^- / CDCl₃ / 1 h / 0 °C

With 1H-imidazole; peracetic acid; trimethylsilyl trifluoromethanesulfonate; mercury(II) diacetate; methyltriphenoxyphosphonium iodide; hydrogen; diisobutylaluminium hydride; palladium on activated charcoal; In chloroform-d1; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ol035581m

Reference yield:

: 623566-47-2
(2S,5S,6S)-6-[2-(dimethylphenylsilyl)vinyl]-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester

: 623566-49-4
tert-butyl (2-((2R,3S,6S)-6-(iodomethyl)-3-methyltetrahydro-2H-pyran-2-yl)ethoxy)diphenylsilane

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / H₂ / Pd/C / ethyl acetate / 18 h / 20 °C / 760 Torr

2: 76 percent / aq. CH₃CO₃H; Hg(OAc)2 / 1 h / 20 °C

3: 99 percent / imidazole / dimethylformamide / 12 h / 0 - 20 °C

4: 90 percent / Dibal-H / CH₂Cl₂; hexane / 2.5 h / 0 °C

5: 86 percent / (PhO)3P⁺CH₃I^- / CDCl₃ / 1 h / 0 °C

With 1H-imidazole; peracetic acid; mercury(II) diacetate; methyltriphenoxyphosphonium iodide; hydrogen; diisobutylaluminium hydride; palladium on activated charcoal; In chloroform-d1; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ol035581m