(2S,3S,6R)-3-benzyloxy-2-(tert-butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosylpiperidine

Base Information

Chemical Name:(2S,3S,6R)-3-benzyloxy-2-(tert-butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosylpiperidine
CAS No.:405506-65-2
Molecular Formula:C₃₈H₄₇NO₅SSi
Molecular Weight:657.946
Hs Code.:

Synonyms:(2S,3S,6R)-3-benzyloxy-2-(tert-butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosylpiperidine

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Chemical Property of (2S,3S,6R)-3-benzyloxy-2-(tert-butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosylpiperidine

Chemical Property:

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Technology Process of (2S,3S,6R)-3-benzyloxy-2-(tert-butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosylpiperidine

There total 1 articles about (2S,3S,6R)-3-benzyloxy-2-(tert-butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosylpiperidine 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%

: 100-39-0
benzyl bromide

: 258531-66-7
(2S,3S,6R)-2-(tert-Butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosylpiperidin-3-ol

: 405506-65-2
(2S,3S,6R)-3-benzyloxy-2-(tert-butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosylpiperidine

Guidance literature:: (2S,3S,6R)-2-(tert-Butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosylpiperidin-3-ol; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.5h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; for 2h;
DOI:10.1055/s-2002-19302

Reference yield:

: 405506-65-2
(2S,3S,6R)-3-benzyloxy-2-(tert-butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosylpiperidine

: 405506-76-5
(2S,3S,6R,4''R)-{6-[10'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)decyl]-2-hydroxymethyl}-1-tosylpiperidin-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 87 percent / TiCl₄ / CH₂Cl₂ / 1.5 h / -78 - 0 °C

2.1: K₃Fe(CN)6; aq. K₂CO₃; CH₃SO₂NH₂ / K₂OsO₂(OH)2 / 2-methyl-propan-2-ol / 1 h / 20 °C

3.1: 115 mg / aq. NaIO₄ / tetrahydrofuran / 0.5 h

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

4.2: 90 percent / tetrahydrofuran; hexane / 1 h / 20 °C

5.1: 93 percent / TBAF / tetrahydrofuran / 12 h / 40 °C

6.1: 85 percent / H₂ / 10 percent Pd/C / methanol / 2 h / 750.06 Torr

With sodium periodate; n-butyllithium; methanesulfonamide; tetrabutyl ammonium fluoride; hydrogen; titanium tetrachloride; potassium carbonate; potassium hexacyanoferrate(III); palladium on activated charcoal; K₂OsO₂(OH)2; In tetrahydrofuran; methanol; hexane; dichloromethane; tert-butyl alcohol;
DOI:10.1055/s-2002-19302

Reference yield:

: 405506-65-2
(2S,3S,6R)-3-benzyloxy-2-(tert-butyldiphenylsilyloxymethyl)-6-ethoxy-1-tosylpiperidine

: 405506-69-6
(2S,3S,6R)-[5-benzyloxy-6-(tert-butyldiphenylsilyloxymethyl)-1-tosylpiperidin-2-yl]acetaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / TiCl₄ / CH₂Cl₂ / 1.5 h / -78 - 0 °C

2: K₃Fe(CN)6; aq. K₂CO₃; CH₃SO₂NH₂ / K₂OsO₂(OH)2 / 2-methyl-propan-2-ol / 1 h / 20 °C

3: 115 mg / aq. NaIO₄ / tetrahydrofuran / 0.5 h

With sodium periodate; methanesulfonamide; titanium tetrachloride; potassium carbonate; potassium hexacyanoferrate(III); K₂OsO₂(OH)2; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;
DOI:10.1055/s-2002-19302