(2S,3R,6S)-6-Allyl-3-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidine

Base Information

Chemical Name:(2S,3R,6S)-6-Allyl-3-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidine
CAS No.:249928-49-2
Molecular Formula:C₃₉H₄₇NO₄SSi
Molecular Weight:653.958
Hs Code.:

Synonyms:(2S,3R,6S)-6-Allyl-3-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidine

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Chemical Property of (2S,3R,6S)-6-Allyl-3-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidine

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Technology Process of (2S,3R,6S)-6-Allyl-3-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidine

There total 7 articles about (2S,3R,6S)-6-Allyl-3-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidine 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: 87.0%

: 249928-48-1
(2S,3R,6S)-3-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-ethoxy-1-(toluene-4-sulfonyl)-piperidine

: 762-72-1
allyl-trimethyl-silane

: 249928-49-2
(2S,3R,6S)-6-Allyl-3-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidine

Guidance literature:: With titanium tetrachloride; In dichloromethane; at -78 ℃;
DOI:10.1016/S0040-4039(99)01387-8

Reference yield:

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

: 249928-49-2
(2S,3R,6S)-6-Allyl-3-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidine

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / m-CPBA / CH₂Cl₂

2: 95 percent / BF₃*OEt₂; 4 Angstroem mol. sieves / tetrahydrofuran / 0 °C

3: 91 percent / H₂ / Pd-C / ethyl acetate

4: 85 percent / NaBH₃CN / acetic acid; methanol / 0 - 20 °C

5: 91 percent / NaH; Bu₄NI / tetrahydrofuran

6: 87 percent / TiCl₄ / CH₂Cl₂ / -78 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetic acid; ethyl acetate; 1: Oxidation / 2: Etherification / 3: Catalytic hydrogenation / 4: Reduction / 5: Etherification / 6: Alkylation;
DOI:10.1016/S0040-4039(99)01387-8

Reference yield:

: 249928-46-9
2-(tert-butyl-diphenyl-silanyloxymethyl)-6-ethoxy-1-(toluene-4-sulfonyl)-1,6-dihydro-2H-pyridin-3-one

: 249928-49-2
(2S,3R,6S)-6-Allyl-3-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidine

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / H₂ / Pd-C / ethyl acetate

2: 85 percent / NaBH₃CN / acetic acid; methanol / 0 - 20 °C

3: 91 percent / NaH; Bu₄NI / tetrahydrofuran

4: 87 percent / TiCl₄ / CH₂Cl₂ / -78 °C

With hydrogen; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetic acid; ethyl acetate; 1: Catalytic hydrogenation / 2: Reduction / 3: Etherification / 4: Alkylation;
DOI:10.1016/S0040-4039(99)01387-8