(2S,3S,6S)-3-Benzyloxy-6-[(Z)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-2-methyl-piperidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,3S,6S)-3-Benzyloxy-6-[(Z)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-2-methyl-piperidine-1-carboxylic acid benzyl ester
• CAS No.: 239802-30-3
• Molecular Formula: C₃₅H₄₉NO₅
• Molecular Weight: 563.778
• Mol file: 239802-30-3.mol

Synonyms:

Chemical Property of (2S,3S,6S)-3-Benzyloxy-6-[(Z)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-2-methyl-piperidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,6S)-3-Benzyloxy-6-[(Z)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-2-methyl-piperidine-1-carboxylic acid benzyl ester

There total 14 articles about (2S,3S,6S)-3-Benzyloxy-6-[(Z)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-2-methyl-piperidine-1-carboxylic acid benzyl ester 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:

benzyl bromide (100-39-0) → (2S,3S,6S)-3-Benzyloxy-6-[(Z)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-2-methyl-piperidine-1-carboxylic acid benzyl ester (239802-30-3)

Guidance literature:

Multi-step reaction with 8 steps

1: NaH / dimethylformamide; benzene / 80 °C

2: 96 percent / Lawesson's reagent / tetrahydrofuran / Heating

3: 83 percent / PPh₃, Et₃N / acetonitrile / Heating

4: H₂ / Pd(OH)2 / methanol

5: K₂CO₃ / CH₂Cl₂; H₂O

6: 90 percent / Super-Hydride / tetrahydrofuran

7: (COCl)2, DMSO, Et₃N

8: n-BuLi / tetrahydrofuran

With Lawessons reagent; n-butyllithium; oxalyl dichloride; hydrogen; sodium hydride; lithium triethylborohydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo990397t

Reference yield:

ethyl 1-benzyl-3,6-dioxo-2-piperidinecarboxylate (92912-21-5) → (2S,3S,6S)-3-Benzyloxy-6-[(Z)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-2-methyl-piperidine-1-carboxylic acid benzyl ester (239802-30-3)

Guidance literature:

Multi-step reaction with 14 steps

1: 88 percent / baker's yeast / H₂O

2: 98 percent / Huenig base / CHCl₃ / Heating

3: 96 percent / Super-Hydride / tetrahydrofuran / 0 °C

4: 95 percent / n-Bu₃P, pyridine

5: 95 percent / Raney Ni (W-4) / ethanol

6: conc. HCl / methanol

7: NaH / dimethylformamide; benzene / 80 °C

8: 96 percent / Lawesson's reagent / tetrahydrofuran / Heating

9: 83 percent / PPh₃, Et₃N / acetonitrile / Heating

10: H₂ / Pd(OH)2 / methanol

11: K₂CO₃ / CH₂Cl₂; H₂O

12: 90 percent / Super-Hydride / tetrahydrofuran

13: (COCl)2, DMSO, Et₃N

14: n-BuLi / tetrahydrofuran

With Lawessons reagent; pyridine; hydrogenchloride; n-butyllithium; baker's yeast; oxalyl dichloride; tributylphosphine; Raney Ni (W-4); hydrogen; sodium hydride; lithium triethylborohydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo990397t

Reference yield:

(5S,6S)-1-Benzyl-5-methoxymethoxy-6-methyl-piperidin-2-one (165672-51-5) → (2S,3S,6S)-3-Benzyloxy-6-[(Z)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-2-methyl-piperidine-1-carboxylic acid benzyl ester (239802-30-3)

Guidance literature:

Multi-step reaction with 9 steps

1: conc. HCl / methanol

2: NaH / dimethylformamide; benzene / 80 °C

3: 96 percent / Lawesson's reagent / tetrahydrofuran / Heating

4: 83 percent / PPh₃, Et₃N / acetonitrile / Heating

5: H₂ / Pd(OH)2 / methanol

6: K₂CO₃ / CH₂Cl₂; H₂O

7: 90 percent / Super-Hydride / tetrahydrofuran

8: (COCl)2, DMSO, Et₃N

9: n-BuLi / tetrahydrofuran

With Lawessons reagent; hydrogenchloride; n-butyllithium; oxalyl dichloride; hydrogen; sodium hydride; lithium triethylborohydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jo990397t

upstream raw materials:

benzyl bromide

ethyl 1-benzyl-3,6-dioxo-2-piperidinecarboxylate

(5S,6S)-1-Benzyl-5-methoxymethoxy-6-methyl-piperidin-2-one

(2R,3S)-1-Benzyl-3-hydroxy-6-oxo-piperidine-2-carboxylic acid ethyl ester