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

Base Information

• Chemical Name: (2S,3R,6S)-3-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-ethoxy-1-(toluene-4-sulfonyl)-piperidine
• CAS No.: 249928-48-1
• Molecular Formula: C₃₈H₄₇NO₅SSi
• Molecular Weight: 657.946
• Mol file: 249928-48-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (2S,3R,6S)-3-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-ethoxy-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: 91.0%

benzyl bromide (100-39-0) + (2S,3R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethoxy-1-(toluene-4-sulfonyl)-piperidin-3-ol → (2S,3R,6S)-3-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-ethoxy-1-(toluene-4-sulfonyl)-piperidine (249928-48-1)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(99)01387-8

Reference yield:

(S)-1-(furan-2-yl)-2-tert-butyldiphenylsilyloxy-N-(toluene-4-sulfonyl)ethylamine (249928-44-7) → (2S,3R,6S)-3-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-ethoxy-1-(toluene-4-sulfonyl)-piperidine (249928-48-1)

Guidance literature:

Multi-step reaction with 5 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

With 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; 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;

DOI:10.1016/S0040-4039(99)01387-8

Reference yield:

2-(tert-butyl-diphenyl-silanyloxymethyl)-6-ethoxy-1-(toluene-4-sulfonyl)-1,6-dihydro-2H-pyridin-3-one (249928-46-9) → (2S,3R,6S)-3-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-ethoxy-1-(toluene-4-sulfonyl)-piperidine (249928-48-1)

Guidance literature:

Multi-step reaction with 3 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

With hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; palladium on activated charcoal; In tetrahydrofuran; methanol; acetic acid; ethyl acetate; 1: Catalytic hydrogenation / 2: Reduction / 3: Etherification;

DOI:10.1016/S0040-4039(99)01387-8

upstream raw materials:

benzyl bromide

(S)-1-(furan-2-yl)-2-tert-butyldiphenylsilyloxy-N-(toluene-4-sulfonyl)ethylamine

(2S,6S)-2-(tert-Butyldiphenylsilyloxymethyl)-6-hydroxy-1-tosyl-1,6-dihydropyridin-3(2H)-one

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

Downstream raw materials:

(2S,3R,6S)-3-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-[(E)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-1-(toluene-4-sulfonyl)-piperidine

12-[(2R,5R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxy-1-(toluene-4-sulfonyl)-piperidin-2-yl]-dodecan-3-one

[(2S,5R,6S)-5-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetaldehyde

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