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

Base Information

• Chemical Name: (5S,6S)-N-benzyl-5-benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-6-methyl-3-(p-toluenesulfonyl)-2,3-dehydropiperidine
• CAS No.: 940899-60-5
• Molecular Formula: C₃₄H₄₅NO₄SSi
• Molecular Weight: 591.887
• Mol file: 940899-60-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (5S,6S)-N-benzyl-5-benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-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:

C34H46ClNO4SSi (940899-58-1) → (5S,6S)-N-benzyl-5-benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-6-methyl-3-(p-toluenesulfonyl)-2,3-dehydropiperidine (940899-60-5)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.0666667h;

DOI:10.1021/jo0703101

Reference yield:

(1S,2R)-N-benzyl-2-benzyloxy-3-chloro-1-methylpropylamine (940899-48-9) → (5S,6S)-N-benzyl-5-benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-6-methyl-3-(p-toluenesulfonyl)-2,3-dehydropiperidine (940899-60-5)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With lithium diisopropyl amide; In tetrahydrofuran; methanol;

DOI:10.1021/jo0703101

Reference yield:

N-[(1S,2S)-2-benzyloxy-1-methylbut-3-enyl]benzamide (940899-53-6) → (5S,6S)-N-benzyl-5-benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-6-methyl-3-(p-toluenesulfonyl)-2,3-dehydropiperidine (940899-60-5)

Guidance literature:

Multi-step reaction with 5 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

With sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; thionyl chloride; N-methyl-2-indolinone; lithium diisopropyl amide; In tetrahydrofuran; methanol; chloroform; water; acetone; tert-butyl alcohol;

DOI:10.1021/jo0703101

upstream raw materials:

C₃₄H₄₆ClNO₄SSi

N-[(1S,2S)-2-benzyloxy-1-methylbut-3-enyl]benzamide

C₁₈H₁₉NO₃

(1S,2R)-N-benzyl-2-benzyloxy-3-chloro-1-methylpropylamine

Downstream raw materials:

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

(5S,6S)-N-benzyl-5-benzyloxy-6-methyl-2,3-dehydropiperidine-2-carbaldehyde

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

(2S,3S,6R)-N-benzyl-3-benzyloxy-6-hydroxymethyl-2-methylpiperidine