dimethyl (3S)-3-(tert-butyldiphenylsilyloxy)-2-oxo-7-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hept-5-ynyl-phosphonate

Base Information

Chemical Name:dimethyl (3S)-3-(tert-butyldiphenylsilyloxy)-2-oxo-7-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hept-5-ynyl-phosphonate
CAS No.:302554-84-3
Molecular Formula:C₃₀H₄₁O₇PSi
Molecular Weight:572.711
Hs Code.:

Synonyms:dimethyl (3S)-3-(tert-butyldiphenylsilyloxy)-2-oxo-7-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hept-5-ynyl-phosphonate

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Chemical Property of dimethyl (3S)-3-(tert-butyldiphenylsilyloxy)-2-oxo-7-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hept-5-ynyl-phosphonate

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Technology Process of dimethyl (3S)-3-(tert-butyldiphenylsilyloxy)-2-oxo-7-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hept-5-ynyl-phosphonate

There total 8 articles about dimethyl (3S)-3-(tert-butyldiphenylsilyloxy)-2-oxo-7-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hept-5-ynyl-phosphonate 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: 91.0%

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

: 756-79-6
dimethyl methane phosphonate

: 302554-84-3
dimethyl (3S)-3-(tert-butyldiphenylsilyloxy)-2-oxo-7-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hept-5-ynyl-phosphonate

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 3h;
DOI:10.1016/S0040-4039(00)00961-8

Reference yield: 70.0%

: 34939-91-8,58648-56-9
dimethyl lithiomethylphosphonate

: tert-butyl-[1-(4-methoxy-phenoxymethyl)-5-(tetrahydro-pyran-2-yloxy)-pent-3-ynyloxy]-diphenyl-silane

: 302554-84-3
dimethyl (3S)-3-(tert-butyldiphenylsilyloxy)-2-oxo-7-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hept-5-ynyl-phosphonate

Guidance literature:: Multistep reaction.;
DOI:10.1002/1615-4169(200208)344:6/7<573::AID-ADSC573>3.0.CO;2-C

Reference yield:

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

: 302554-84-3
dimethyl (3S)-3-(tert-butyldiphenylsilyloxy)-2-oxo-7-[(2R,S)-tetrahydro-2H-pyran-2-yloxy]-hept-5-ynyl-phosphonate

Guidance literature:: Multi-step reaction with 3 steps

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

2.1: 1.71 g / diethyl ether

3.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C

With sodium chlorite; dipotassium hydrogenphosphate; n-butyllithium; 2,3-Dimethyl-2-butene; In tetrahydrofuran; diethyl ether; hexane; tert-butyl alcohol; 1.1: Pinnick oxidation;
DOI:10.1021/jo026743f