(2S,3S,2''R,3''S)-p-toluenesulfonic acid 3-[3''-(tert-butyldimethylsiloxy)tetrahydropyran-2''-yl-methyl]-oxiran-2-yl-methyl ester

Base Information

Chemical Name:(2S,3S,2''R,3''S)-p-toluenesulfonic acid 3-[3''-(tert-butyldimethylsiloxy)tetrahydropyran-2''-yl-methyl]-oxiran-2-yl-methyl ester
CAS No.:245676-75-9
Molecular Formula:C₂₂H₃₆O₆SSi
Molecular Weight:456.676
Hs Code.:

Synonyms:(2S,3S,2''R,3''S)-p-toluenesulfonic acid 3-[3''-(tert-butyldimethylsiloxy)tetrahydropyran-2''-yl-methyl]-oxiran-2-yl-methyl ester

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Chemical Property of (2S,3S,2''R,3''S)-p-toluenesulfonic acid 3-[3''-(tert-butyldimethylsiloxy)tetrahydropyran-2''-yl-methyl]-oxiran-2-yl-methyl ester

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Technology Process of (2S,3S,2''R,3''S)-p-toluenesulfonic acid 3-[3''-(tert-butyldimethylsiloxy)tetrahydropyran-2''-yl-methyl]-oxiran-2-yl-methyl ester

There total 5 articles about (2S,3S,2''R,3''S)-p-toluenesulfonic acid 3-[3''-(tert-butyldimethylsiloxy)tetrahydropyran-2''-yl-methyl]-oxiran-2-yl-methyl 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: 93.0%

: 98-59-9
p-toluenesulfonyl chloride

: 121353-80-8
(2S,3S,2''R,3''S)-{3-[3''-(tert-butyldimethylsiloxy)tetrahydropyran-2''-yl-methyl]-oxiran-2-yl}-methanol

: 245676-75-9
(2S,3S,2''R,3''S)-p-toluenesulfonic acid 3-[3''-(tert-butyldimethylsiloxy)tetrahydropyran-2''-yl-methyl]-oxiran-2-yl-methyl ester

Guidance literature:: With 4-diphenylacetoxy-N-methylpiperidine methiodide; triethylamine; In dichloromethane; at 25 ℃; for 8h;
DOI:10.1016/S0040-4020(02)00047-9

Reference yield:

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

: 245676-75-9
(2S,3S,2''R,3''S)-p-toluenesulfonic acid 3-[3''-(tert-butyldimethylsiloxy)tetrahydropyran-2''-yl-methyl]-oxiran-2-yl-methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 88 percent / NaH / benzene / 0.25 h / 25 °C

2.1: 98 percent / DIBALH / hexane; diethyl ether / 1 h / 0 °C

3.1: (+)-diethyl-D-tartrate; 4 Angstroem molecular sieves; titanium isopropoxide / CH₂Cl₂; decane / 1 h / -20 °C

3.2: 95 percent / tert-butyl hydroperoxide / CH₂Cl₂; decane / 12 h / -20 °C

4.1: 93 percent / 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 9 h / 0 - 25 °C

With titanium(IV) isopropylate; dmap; (+)-diethyl-D-tartrate; 4 A molecular sieve; sodium hydride; diisobutylaluminium hydride; triethylamine; In diethyl ether; decane; hexane; dichloromethane; benzene;
DOI:10.1021/ol990618h

Reference yield:

: 175664-06-9
(2R,3S)-2-(2',2'-dibromovinyl)-3-(tert-butyldimethylsiloxy)-tetrahydropyran

: 245676-75-9
(2S,3S,2''R,3''S)-p-toluenesulfonic acid 3-[3''-(tert-butyldimethylsiloxy)tetrahydropyran-2''-yl-methyl]-oxiran-2-yl-methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 82 percent / n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

2.1: BH₃*SMe₂; 2-methyl-2-butene / tetrahydrofuran / 12 h / 25 °C

2.2: 88 percent / aq. NaOH; hydrogen peroxide / tetrahydrofuran / 2 h / 0 °C

3.1: 88 percent / NaH / benzene / 0.25 h / 25 °C

4.1: 98 percent / DIBALH / hexane; diethyl ether / 1 h / 0 °C

5.1: (+)-diethyl-D-tartrate; 4 Angstroem molecular sieves; titanium isopropoxide / CH₂Cl₂; decane / 1 h / -20 °C

5.2: 95 percent / tert-butyl hydroperoxide / CH₂Cl₂; decane / 12 h / -20 °C

6.1: 93 percent / 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 9 h / 0 - 25 °C

With titanium(IV) isopropylate; dmap; n-butyllithium; 2-methyl-but-2-ene; dimethylsulfide borane complex; (+)-diethyl-D-tartrate; 4 A molecular sieve; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; decane; hexane; dichloromethane; benzene;
DOI:10.1021/ol990618h