(2'R,3'R,4R,5S)-2,2-dimethyl-5-<(tert-butyldimethylsilyloxy)methyl>-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane

Base Information

Chemical Name:(2'R,3'R,4R,5S)-2,2-dimethyl-5-<(tert-butyldimethylsilyloxy)methyl>-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane
CAS No.:157661-83-1
Molecular Formula:C₂₁H₃₃NO₆SSi
Molecular Weight:455.648
Hs Code.:

Synonyms:(2'R,3'R,4R,5S)-2,2-dimethyl-5-<(tert-butyldimethylsilyloxy)methyl>-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane

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Chemical Property of (2'R,3'R,4R,5S)-2,2-dimethyl-5-<(tert-butyldimethylsilyloxy)methyl>-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane

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Technology Process of (2'R,3'R,4R,5S)-2,2-dimethyl-5-<(tert-butyldimethylsilyloxy)methyl>-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane

There total 5 articles about (2'R,3'R,4R,5S)-2,2-dimethyl-5-<(tert-butyldimethylsilyloxy)methyl>-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane 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: 67.0%

: 157661-82-0
Z-(4S,5S)-2,2-dimethyl-5-<(tert-butyldimethylsilyloxy)methyl>-4-<2'-<(4''-methylphenyl)thio>-2'-nitroethenyl>-1,3-dioxolane

: 157661-83-1
(2'R,3'R,4R,5S)-2,2-dimethyl-5-<(tert-butyldimethylsilyloxy)methyl>-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane

Guidance literature:: With tert.-butylhydroperoxide; potassium hydride; In tetrahydrofuran; paraffin; at -78 ℃; for 1h;
DOI:10.1021/jo00125a032

Reference yield:

: 157661-82-0
Z-(4S,5S)-2,2-dimethyl-5-<(tert-butyldimethylsilyloxy)methyl>-4-<2'-<(4''-methylphenyl)thio>-2'-nitroethenyl>-1,3-dioxolane

: 157661-83-1
(2'R,3'R,4R,5S)-2,2-dimethyl-5-<(tert-butyldimethylsilyloxy)methyl>-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane

: 157661-86-4
(2'S,3'S,4R,5S)-2,2-dimethyl-5-<(tert-butyldimethylsilyloxy)methyl>-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane

Guidance literature:: With potassium tert-butylperoxide; In tetrahydrofuran; at -78 ℃; for 2h; Yield given. Yields of byproduct given;
DOI:10.1039/c39940000095

Reference yield:

: 108817-97-6
(4R,5S)-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

: 157661-83-1
(2'R,3'R,4R,5S)-2,2-dimethyl-5-<(tert-butyldimethylsilyloxy)methyl>-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) t-BuOK, t-BuOH, 2.) MeSO₂Cl, i-Pr₂NEt / 1.) THF, room temperature, 2.5 h, 2.) CH₂Cl₂, -78 to room temperature, 2 h

2: n-BuLi, t-BuOOH / toluene; tetrahydrofuran / 1 h / -78 °C

With tert.-butylhydroperoxide; n-butyllithium; potassium tert-butylate; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; tert-butyl alcohol; In tetrahydrofuran; toluene;
DOI:10.1021/jo00125a032