(E)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone

Base Information

Chemical Name:(E)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone
CAS No.:1338565-59-5
Molecular Formula:C₂₀H₃₂O₄SSi
Molecular Weight:396.623
Hs Code.:

Synonyms:(E)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone

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Chemical Property of (E)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone

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Technology Process of (E)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone

There total 2 articles about (E)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone 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: 68.0%

: 17872-92-3
(phenylsulfonylmethyl)trimethylsilane

: 125878-02-6
2-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)acetaldehyde

: 1338565-58-4
(Z)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone

: 1338565-59-5
(E)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone

Guidance literature:: (phenylsulfonylmethyl)trimethylsilane; With n-butyllithium; In 1,2-dimethoxyethane; hexane; at -80 ℃; for 0.5h; Inert atmosphere;

2-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)acetaldehyde; In 1,2-dimethoxyethane; hexane; at -80 ℃; for 0.5h; optical yield given as %de; Inert atmosphere;
DOI:10.1021/ol202467z

Reference yield:

: 441351-08-2
tert-Butyl-((2R,3S)-2-[1,3]dithian-2-ylmethyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane

: 1338565-59-5
(E)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone

Guidance literature:: Multi-step reaction with 2 steps

1.1: mercury(II) perchlorate; calcium carbonate / tetrahydrofuran; water / 2 h / 20 °C

2.1: n-butyllithium / 1,2-dimethoxyethane; hexane / 0.5 h / -80 °C / Inert atmosphere

2.2: 0.5 h / -80 °C / Inert atmosphere

With n-butyllithium; mercury(II) perchlorate; calcium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; water;
DOI:10.1021/ol202467z

Reference yield: 83.0%

: 1338565-59-5
(E)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone

: trans-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)-1,2-epoxypropan-1-yl phenyl sulfone

Guidance literature:: With tert.-butylhydroperoxide; potassium tert-butylate; In tetrahydrofuran; 2,2'-oxybis(2-methyl-propane); at -80 - -25 ℃; for 23h; optical yield given as %de;
DOI:10.1021/ol202467z