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

Base Information

Chemical Name:(5S,6S)-N-benzyl-5-benzyloxy-2-hydroxymethyl-6-methyl-3-(p-toluenesulfonyl)-2,3-dehydropiperidine
CAS No.:940899-46-7
Molecular Formula:C₂₈H₃₁NO₄S
Molecular Weight:477.624
Hs Code.:

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

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

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

There total 9 articles about (5S,6S)-N-benzyl-5-benzyloxy-2-hydroxymethyl-6-methyl-3-(p-toluenesulfonyl)-2,3-dehydropiperidine 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%

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

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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1021/jo0703101

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

With tetrabutyl ammonium fluoride; lithium diisopropyl amide; In tetrahydrofuran; methanol;
DOI:10.1021/jo0703101

Reference yield:

: 940899-53-6
N-[(1S,2S)-2-benzyloxy-1-methylbut-3-enyl]benzamide

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

Guidance literature:: Multi-step reaction with 6 steps

1: NaIO₄; NMO; OsO₄ / 2-methyl-propan-2-ol; acetone; H₂O / 10 h / 20 °C

2: 89 percent / LAH / tetrahydrofuran / 10 h / Heating

3: 79 percent / SOCl₂ / CHCl₃ / 72 h / 48 °C

4: 79 percent / methanol / 20 h / 20 °C

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

6: 91 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

With sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; thionyl chloride; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; lithium diisopropyl amide; In tetrahydrofuran; methanol; chloroform; water; acetone; tert-butyl alcohol;
DOI:10.1021/jo0703101