(3R,6S)-[6-(tert-butyldiphenylsilanyloxymethyl)-2,5-dioxo-1-(toluene-4-sulfonyl)piperidin-3-yl]carbamic acid benzyl ester

Base Information

Chemical Name:(3R,6S)-[6-(tert-butyldiphenylsilanyloxymethyl)-2,5-dioxo-1-(toluene-4-sulfonyl)piperidin-3-yl]carbamic acid benzyl ester
CAS No.:381733-38-6
Molecular Formula:C₃₇H₄₀N₂O₇SSi
Molecular Weight:684.885
Hs Code.:

Synonyms:(3R,6S)-[6-(tert-butyldiphenylsilanyloxymethyl)-2,5-dioxo-1-(toluene-4-sulfonyl)piperidin-3-yl]carbamic acid benzyl ester

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Chemical Property of (3R,6S)-[6-(tert-butyldiphenylsilanyloxymethyl)-2,5-dioxo-1-(toluene-4-sulfonyl)piperidin-3-yl]carbamic acid benzyl ester

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Technology Process of (3R,6S)-[6-(tert-butyldiphenylsilanyloxymethyl)-2,5-dioxo-1-(toluene-4-sulfonyl)piperidin-3-yl]carbamic acid benzyl ester

There total 4 articles about (3R,6S)-[6-(tert-butyldiphenylsilanyloxymethyl)-2,5-dioxo-1-(toluene-4-sulfonyl)piperidin-3-yl]carbamic acid benzyl 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: 80.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: (3R,6S)-3-Amino-6-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidine-2,5-dione

: 381733-38-6
(3R,6S)-[6-(tert-butyldiphenylsilanyloxymethyl)-2,5-dioxo-1-(toluene-4-sulfonyl)piperidin-3-yl]carbamic acid benzyl ester

Guidance literature:: With acetic acid; triethylamine; In dichloromethane; for 0.5h; pH=8;
DOI:10.1021/jo0159688

Reference yield:

: 249928-44-7
(S)-1-(furan-2-yl)-2-tert-butyldiphenylsilyloxy-N-(toluene-4-sulfonyl)ethylamine

: 381733-38-6
(3R,6S)-[6-(tert-butyldiphenylsilanyloxymethyl)-2,5-dioxo-1-(toluene-4-sulfonyl)piperidin-3-yl]carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: m-CPBA / CH₂Cl₂ / 2 h

1.2: Jones reagent / acetone / 0.33 h / 0 °C

2.1: 72 percent / NaN₃; NaOAc; AcOH / methanol / 12 h

3.1: Zn; AcOH / CH₂Cl₂ / 0.5 h / 35 °C / ultrasonication

4.1: 80 percent / Et₃N; AcOH / CH₂Cl₂ / 0.5 h / pH 8

With sodium azide; sodium acetate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In methanol; dichloromethane;
DOI:10.1021/jo0159688

Reference yield:

: 381733-31-9
(S)-6-(tert-butyldiphenylsilanyloxymethyl)-1-(toluene-4-sulfonyl)-1,6-dihydropyridine-2,5-dione

: 381733-38-6
(3R,6S)-[6-(tert-butyldiphenylsilanyloxymethyl)-2,5-dioxo-1-(toluene-4-sulfonyl)piperidin-3-yl]carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 72 percent / NaN₃; NaOAc; AcOH / methanol / 12 h

2: Zn; AcOH / CH₂Cl₂ / 0.5 h / 35 °C / ultrasonication

3: 80 percent / Et₃N; AcOH / CH₂Cl₂ / 0.5 h / pH 8

With sodium azide; sodium acetate; acetic acid; triethylamine; zinc; In methanol; dichloromethane;
DOI:10.1021/jo0159688