(2S,5S,6S)-N-benzyl-5-benzyloxy-2-hydroxymethyl-6-methyl-3-(p-toluenesulfonyl)piperidine

Base Information

Chemical Name:(2S,5S,6S)-N-benzyl-5-benzyloxy-2-hydroxymethyl-6-methyl-3-(p-toluenesulfonyl)piperidine
CAS No.:940899-62-7
Molecular Formula:C₂₈H₃₃NO₄S
Molecular Weight:479.64
Hs Code.:

Synonyms:(2S,5S,6S)-N-benzyl-5-benzyloxy-2-hydroxymethyl-6-methyl-3-(p-toluenesulfonyl)piperidine

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Chemical Property of (2S,5S,6S)-N-benzyl-5-benzyloxy-2-hydroxymethyl-6-methyl-3-(p-toluenesulfonyl)piperidine

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Technology Process of (2S,5S,6S)-N-benzyl-5-benzyloxy-2-hydroxymethyl-6-methyl-3-(p-toluenesulfonyl)piperidine

There total 10 articles about (2S,5S,6S)-N-benzyl-5-benzyloxy-2-hydroxymethyl-6-methyl-3-(p-toluenesulfonyl)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: 84.0%

: 940899-46-7
(5S,6S)-N-benzyl-5-benzyloxy-2-hydroxymethyl-6-methyl-3-(p-toluenesulfonyl)-2,3-dehydropiperidine

: 940899-62-7
(2S,5S,6S)-N-benzyl-5-benzyloxy-2-hydroxymethyl-6-methyl-3-(p-toluenesulfonyl)piperidine

: (5S,6S)-N-benzyl-5-benzyloxy-2-hydroxymethyl-6-methyl-3-(p-toluenesulfonyl)piperidine

Guidance literature:: With sodium cyanoborohydride; trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 2h;
DOI:10.1021/jo0703101

Reference yield:

: 940899-60-5
(5S,6S)-N-benzyl-5-benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-6-methyl-3-(p-toluenesulfonyl)-2,3-dehydropiperidine

: 940899-62-7
(2S,5S,6S)-N-benzyl-5-benzyloxy-2-hydroxymethyl-6-methyl-3-(p-toluenesulfonyl)piperidine

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

2: 84 percent / NaCNBH₃; TFA / CH₂Cl₂ / 2 h / 0 - 20 °C

With tetrabutyl ammonium fluoride; sodium cyanoborohydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo0703101

Reference yield:

: 940899-48-9
(1S,2R)-N-benzyl-2-benzyloxy-3-chloro-1-methylpropylamine

: 940899-62-7
(2S,5S,6S)-N-benzyl-5-benzyloxy-2-hydroxymethyl-6-methyl-3-(p-toluenesulfonyl)piperidine

Guidance literature:: Multi-step reaction with 4 steps

1: 79 percent / methanol / 20 h / 20 °C

2: LDA / tetrahydrofuran / 0.07 h / -78 °C

3: 91 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

4: 84 percent / NaCNBH₃; TFA / CH₂Cl₂ / 2 h / 0 - 20 °C

With tetrabutyl ammonium fluoride; sodium cyanoborohydride; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo0703101