(4aS,6S,8aR)-5-Benzyl-6-[(Z)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine

Base Information

Chemical Name:(4aS,6S,8aR)-5-Benzyl-6-[(Z)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine
CAS No.:239802-33-6
Molecular Formula:C₃₀H₄₇NO₄
Molecular Weight:485.707
Hs Code.:

Synonyms:

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Chemical Property of (4aS,6S,8aR)-5-Benzyl-6-[(Z)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine

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Technology Process of (4aS,6S,8aR)-5-Benzyl-6-[(Z)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine

There total 13 articles about (4aS,6S,8aR)-5-Benzyl-6-[(Z)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine 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:

: 92912-21-5
ethyl 1-benzyl-3,6-dioxo-2-piperidinecarboxylate

: 239802-33-6
(4aS,6S,8aR)-5-Benzyl-6-[(Z)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine

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: 96 percent / NaH / dimethylformamide; benzene

5: conc. HCl / methanol / Heating

6: PCC, AcONa / CH₂Cl₂

7: 1.) H₂, 2.) NaB(OAc)3H / 1.) Pd(OH)2 / 1.) MeOH, 2.) AcOH

8: 91 percent / p-TsOH, MS 5A / CH₂Cl₂ / Ambient temperature

9: 57 percent / Lawesson's reagent / tetrahydrofuran / Heating

10: 72 percent / PPh₃, Et₃N / acetonitrile / Heating

11: 59 percent / NaBH₃CN, TFA / 0 °C

12: 99 percent / LiAlH₄ / tetrahydrofuran / Heating

13: (COCl)2, DMSO, Et₃N

14: n-BuLi / tetrahydrofuran

With Lawessons reagent; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; baker's yeast; oxalyl dichloride; hydrogen; sodium acetate; sodium tris(acetoxy)borohydride; sodium hydride; lithium triethylborohydride; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jo990397t

Reference yield:

: 165672-46-8
(2R,3S)-1-Benzyl-3-hydroxy-6-oxo-piperidine-2-carboxylic acid ethyl ester

: 239802-33-6
(4aS,6S,8aR)-5-Benzyl-6-[(Z)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine

Guidance literature:: Multi-step reaction with 13 steps

1: 98 percent / Huenig base / CHCl₃ / Heating

2: 96 percent / Super-Hydride / tetrahydrofuran / 0 °C

3: 96 percent / NaH / dimethylformamide; benzene

4: conc. HCl / methanol / Heating

5: PCC, AcONa / CH₂Cl₂

6: 1.) H₂, 2.) NaB(OAc)3H / 1.) Pd(OH)2 / 1.) MeOH, 2.) AcOH

7: 91 percent / p-TsOH, MS 5A / CH₂Cl₂ / Ambient temperature

8: 57 percent / Lawesson's reagent / tetrahydrofuran / Heating

9: 72 percent / PPh₃, Et₃N / acetonitrile / Heating

10: 59 percent / NaBH₃CN, TFA / 0 °C

11: 99 percent / LiAlH₄ / tetrahydrofuran / Heating

12: (COCl)2, DMSO, Et₃N

13: n-BuLi / tetrahydrofuran

With Lawessons reagent; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; hydrogen; sodium acetate; sodium tris(acetoxy)borohydride; sodium hydride; lithium triethylborohydride; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jo990397t

Reference yield:

: (5S,6S)-1-Benzyl-6-benzyloxymethyl-5-hydroxy-piperidin-2-one

: 239802-33-6
(4aS,6S,8aR)-5-Benzyl-6-[(Z)-9-(2-ethyl-[1,3]dioxolan-2-yl)-non-2-enyl]-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyridine

Guidance literature:: Multi-step reaction with 9 steps

1: PCC, AcONa / CH₂Cl₂

2: 1.) H₂, 2.) NaB(OAc)3H / 1.) Pd(OH)2 / 1.) MeOH, 2.) AcOH

3: 91 percent / p-TsOH, MS 5A / CH₂Cl₂ / Ambient temperature

4: 57 percent / Lawesson's reagent / tetrahydrofuran / Heating

5: 72 percent / PPh₃, Et₃N / acetonitrile / Heating

6: 59 percent / NaBH₃CN, TFA / 0 °C

7: 99 percent / LiAlH₄ / tetrahydrofuran / Heating

8: (COCl)2, DMSO, Et₃N

9: n-BuLi / tetrahydrofuran

With Lawessons reagent; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; hydrogen; sodium acetate; sodium tris(acetoxy)borohydride; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo990397t