(1'S,2R,3R)-3-<1'-(tert-butoxydimethylsilyloxy)ethyl>-2-(4''-methylphenylthio)-2-nitrooxirane

Base Information

Chemical Name:(1'S,2R,3R)-3-<1'-(tert-butoxydimethylsilyloxy)ethyl>-2-(4''-methylphenylthio)-2-nitrooxirane
CAS No.:160401-33-2
Molecular Formula:C₁₇H₂₇NO₄SSi
Molecular Weight:369.557
Hs Code.:

Synonyms:(1'S,2R,3R)-3-<1'-(tert-butoxydimethylsilyloxy)ethyl>-2-(4''-methylphenylthio)-2-nitrooxirane

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Chemical Property of (1'S,2R,3R)-3-<1'-(tert-butoxydimethylsilyloxy)ethyl>-2-(4''-methylphenylthio)-2-nitrooxirane

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Technology Process of (1'S,2R,3R)-3-<1'-(tert-butoxydimethylsilyloxy)ethyl>-2-(4''-methylphenylthio)-2-nitrooxirane

There total 7 articles about (1'S,2R,3R)-3-<1'-(tert-butoxydimethylsilyloxy)ethyl>-2-(4''-methylphenylthio)-2-nitrooxirane 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: 83.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 160349-82-6
(1'S,2R,3R)-3-(1'-hydroxyethyl)-2-(4''-methylphenylthio)-2-nitrooxirane

: 160401-33-2
(1'S,2R,3R)-3-<1'-(tert-butoxydimethylsilyloxy)ethyl>-2-(4''-methylphenylthio)-2-nitrooxirane

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 2.5h;

Reference yield:

: 160349-77-9
(1Z,3S)-3-tert-butyldimethylsilyloxy-1-(4'-methylphenylthio)-1-nitrobut-1-ene

: 160401-33-2
(1'S,2R,3R)-3-<1'-(tert-butoxydimethylsilyloxy)ethyl>-2-(4''-methylphenylthio)-2-nitrooxirane

: (1'S,2S,3S)-3-<1'-(tert-butoxydimethylsilyloxy)ethyl>-2-(4''-methylphenylthio)-2-nitrooxirane

Guidance literature:: With trityl hydroperoxide; potassium hydride; In tetrahydrofuran; at -78 - -60 ℃; for 0.166667h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;

Reference yield:

: 150640-22-5
<(4-methylphenyl)thio>nitromethane

: 160401-33-2
(1'S,2R,3R)-3-<1'-(tert-butoxydimethylsilyloxy)ethyl>-2-(4''-methylphenylthio)-2-nitrooxirane

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) BuLi, 2.) Ac₂O / 1.) THF, hexane, -90 to -78 deg C, 1 h; -78 deg C, 3 h, 2.) THF, hexane, -78 deg C to r.t.

2: 73 percent / BF₃*Et₂O / CH₂Cl₂ / 1.) -78 deg C to r.t., 2 h, 2.) r.t., 2 h

3: 65 percent / tert-BuOOH, BuLi / tetrahydrofuran / 0.17 h / -78 °C

4: 83 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / -78 °C

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; n-butyllithium; boron trifluoride diethyl etherate; acetic anhydride; In tetrahydrofuran; dichloromethane;