tert-butyl (2R,3S)-3-methoxymethoxy-2-[4-(p-toluenesulfonyloxy)butyl]piperidine-1-carboxylate

Base Information

Chemical Name:tert-butyl (2R,3S)-3-methoxymethoxy-2-[4-(p-toluenesulfonyloxy)butyl]piperidine-1-carboxylate
CAS No.:908599-49-5
Molecular Formula:C₂₃H₃₇NO₇S
Molecular Weight:471.615
Hs Code.:

Synonyms:tert-butyl (2R,3S)-3-methoxymethoxy-2-[4-(p-toluenesulfonyloxy)butyl]piperidine-1-carboxylate

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Chemical Property of tert-butyl (2R,3S)-3-methoxymethoxy-2-[4-(p-toluenesulfonyloxy)butyl]piperidine-1-carboxylate

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Technology Process of tert-butyl (2R,3S)-3-methoxymethoxy-2-[4-(p-toluenesulfonyloxy)butyl]piperidine-1-carboxylate

There total 12 articles about tert-butyl (2R,3S)-3-methoxymethoxy-2-[4-(p-toluenesulfonyloxy)butyl]piperidine-1-carboxylate 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: 78.0%

: 908599-47-3
tert-butyl (2R,3S)-2-(4-hydroxybutyl)-3-methoxymethoxypiperidine-1-carboxylate

: 98-59-9
p-toluenesulfonyl chloride

: 908599-49-5
tert-butyl (2R,3S)-3-methoxymethoxy-2-[4-(p-toluenesulfonyloxy)butyl]piperidine-1-carboxylate

Guidance literature:: With pyridine; at 20 ℃; for 1.5h;
DOI:10.1021/jm0601809

Reference yield:

: (S)-5-((R)-1-Amino-3-hydroxy-propyl)-tetrahydro-furan-2-ol

: 908599-49-5
tert-butyl (2R,3S)-3-methoxymethoxy-2-[4-(p-toluenesulfonyloxy)butyl]piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 1.03 g / Et₃N / methanol / 1 h / 20 °C

2.1: 82 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

3.1: iPr₂NEt / 1,2-dimethoxy-ethane / 15 h / 50 °C

4.1: 1.03 g / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂; H₂O / 0.5 h

6.1: NaH / toluene / 15 h / 0 °C

6.2: 399 mg / toluene / 1.5 h / 20 °C

7.1: H₂ / Pd(OH)2/C / tetrahydrofuran / 1 h / 20 °C

8.1: 144 mg / DIBAL-H / toluene / 2 h / -78 °C

9.1: 78 percent / pyridine / 1.5 h / 20 °C

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; toluene; 6.1: Horner-Emmons reaction;
DOI:10.1021/jm0601809

Reference yield:

: 908599-01-9
tert-butyl (2R,3S)-3-hydroxy-2-(2-hydroxyethyl)piperidine-1-carboxylate

: 908599-49-5
tert-butyl (2R,3S)-3-methoxymethoxy-2-[4-(p-toluenesulfonyloxy)butyl]piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 82 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

2.1: iPr₂NEt / 1,2-dimethoxy-ethane / 15 h / 50 °C

3.1: 1.03 g / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

4.1: Dess-Martin periodinane / CH₂Cl₂; H₂O / 0.5 h

5.1: NaH / toluene / 15 h / 0 °C

5.2: 399 mg / toluene / 1.5 h / 20 °C

6.1: H₂ / Pd(OH)2/C / tetrahydrofuran / 1 h / 20 °C

7.1: 144 mg / DIBAL-H / toluene / 2 h / -78 °C

8.1: 78 percent / pyridine / 1.5 h / 20 °C

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; toluene; 5.1: Horner-Emmons reaction;
DOI:10.1021/jm0601809