Methyl (2E)-2-[(5R,6S)-5-(acetyloxy)-6-[(acetyloxy)methyl]-1-(phenylmethyl)-2-piperidinylidene]acetate

Base Information

Chemical Name:Methyl (2E)-2-[(5R,6S)-5-(acetyloxy)-6-[(acetyloxy)methyl]-1-(phenylmethyl)-2-piperidinylidene]acetate
CAS No.:179536-72-2
Molecular Formula:C₂₀H₂₅NO₆
Molecular Weight:375.422
Hs Code.:
DSSTox Substance ID:DTXSID701112223

Synonyms:DTXSID701112223;179536-72-2;Methyl (2E)-2-[(5R,6S)-5-(acetyloxy)-6-[(acetyloxy)methyl]-1-(phenylmethyl)-2-piperidinylidene]acetate

Suppliers and Price of Methyl (2E)-2-[(5R,6S)-5-(acetyloxy)-6-[(acetyloxy)methyl]-1-(phenylmethyl)-2-piperidinylidene]acetate

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of Methyl (2E)-2-[(5R,6S)-5-(acetyloxy)-6-[(acetyloxy)methyl]-1-(phenylmethyl)-2-piperidinylidene]acetate

Chemical Property:

XLogP3:2.3
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:9
Exact Mass:375.16818752
Heavy Atom Count:27
Complexity:567

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC(=O)OCC1C(CCC(=CC(=O)OC)N1CC2=CC=CC=C2)OC(=O)C
Isomeric SMILES:CC(=O)OC[C@H]1[C@@H](CC/C(=C\C(=O)OC)/N1CC2=CC=CC=C2)OC(=O)C

Technology Process of Methyl (2E)-2-[(5R,6S)-5-(acetyloxy)-6-[(acetyloxy)methyl]-1-(phenylmethyl)-2-piperidinylidene]acetate

There total 10 articles about Methyl (2E)-2-[(5R,6S)-5-(acetyloxy)-6-[(acetyloxy)methyl]-1-(phenylmethyl)-2-piperidinylidene]acetate 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: 92.0%

: 96-32-2
bromoacetic acid methyl ester

: 179536-89-1
Acetic acid (2S,3R)-2-acetoxymethyl-1-benzyl-6-thioxo-piperidin-3-yl ester

: 179536-72-2
[(5R,6S)-5-Acetoxy-6-acetoxymethyl-1-benzyl-piperidin-(2E)-ylidene]-acetic acid methyl ester

Guidance literature:: With triethylamine; triphenylphosphine; In acetonitrile; Heating;
DOI:10.1021/jo990397t

Reference yield:

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

: 179536-72-2
[(5R,6S)-5-Acetoxy-6-acetoxymethyl-1-benzyl-piperidin-(2E)-ylidene]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 10 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: 88 percent / pyridine

9: 99 percent / Lawesson's reagent / tetrahydrofuran / Heating

10: 92 percent / PPh₃, Et₃N / acetonitrile / Heating

With Lawessons reagent; pyridine; hydrogenchloride; baker's yeast; hydrogen; sodium acetate; sodium tris(acetoxy)borohydride; sodium hydride; lithium triethylborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; pyridinium chlorochromate; 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

: 179536-72-2
[(5R,6S)-5-Acetoxy-6-acetoxymethyl-1-benzyl-piperidin-(2E)-ylidene]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 9 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: 88 percent / pyridine

8: 99 percent / Lawesson's reagent / tetrahydrofuran / Heating

9: 92 percent / PPh₃, Et₃N / acetonitrile / Heating

With Lawessons reagent; pyridine; hydrogenchloride; hydrogen; sodium acetate; sodium tris(acetoxy)borohydride; sodium hydride; lithium triethylborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; pyridinium chlorochromate; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jo990397t