(4R)-3-[(2R,3S,5E,8E,10E,14S)-15-allyloxycarbonylamino-3-(1-ethoxyethoxy)-2,6,8,14-tetramethylpentadeca-5,8,10-trienoyl]-4-benzyloxazolidin-2-one

Base Information

Chemical Name:(4R)-3-[(2R,3S,5E,8E,10E,14S)-15-allyloxycarbonylamino-3-(1-ethoxyethoxy)-2,6,8,14-tetramethylpentadeca-5,8,10-trienoyl]-4-benzyloxazolidin-2-one
CAS No.:444989-34-8
Molecular Formula:C₃₇H₅₄N₂O₇
Molecular Weight:638.845
Hs Code.:

Synonyms:(4R)-3-[(2R,3S,5E,8E,10E,14S)-15-allyloxycarbonylamino-3-(1-ethoxyethoxy)-2,6,8,14-tetramethylpentadeca-5,8,10-trienoyl]-4-benzyloxazolidin-2-one

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Chemical Property of (4R)-3-[(2R,3S,5E,8E,10E,14S)-15-allyloxycarbonylamino-3-(1-ethoxyethoxy)-2,6,8,14-tetramethylpentadeca-5,8,10-trienoyl]-4-benzyloxazolidin-2-one

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Technology Process of (4R)-3-[(2R,3S,5E,8E,10E,14S)-15-allyloxycarbonylamino-3-(1-ethoxyethoxy)-2,6,8,14-tetramethylpentadeca-5,8,10-trienoyl]-4-benzyloxazolidin-2-one

There total 21 articles about (4R)-3-[(2R,3S,5E,8E,10E,14S)-15-allyloxycarbonylamino-3-(1-ethoxyethoxy)-2,6,8,14-tetramethylpentadeca-5,8,10-trienoyl]-4-benzyloxazolidin-2-one 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: 86.0%

: 109-92-2,25104-37-4
ethyl vinyl ether

: 444989-33-7
(4R)-3-[(2R,3S,5E,8E,10E,14S)-15-allyloxycarbonylamino-3-hydroxy-2,6,8,14-tetramethylpentadeca-5,8,10-trienoyl]-4-benzyloxazolidin-2-one

: 444989-34-8
(4R)-3-[(2R,3S,5E,8E,10E,14S)-15-allyloxycarbonylamino-3-(1-ethoxyethoxy)-2,6,8,14-tetramethylpentadeca-5,8,10-trienoyl]-4-benzyloxazolidin-2-one

Guidance literature:: With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1039/b111146a

Reference yield:

: 116370-25-3
(S)-tert-butyl ((3,7-dimethyloct-6-en-1-yl)oxy)dimethylsilane

: 444989-34-8
(4R)-3-[(2R,3S,5E,8E,10E,14S)-15-allyloxycarbonylamino-3-(1-ethoxyethoxy)-2,6,8,14-tetramethylpentadeca-5,8,10-trienoyl]-4-benzyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 14 steps

1.1: O₃; pyridine / CH₂Cl₂; methanol / -78 °C

1.2: 94 percent / Me₂S / CH₂Cl₂; methanol / 18 h / -78 - 20 °C

2.1: PPh₃; pyridine / CH₂Cl₂ / 0.17 h / 0 °C

2.2: 93 percent / CH₂Cl₂ / 2 h / 0 °C

3.1: 88 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 - 20 °C

4.1: tetrahydrofuran / 3 h / Heating

5.1: 17.86 g / aq. NaOH / Pd(PPh₃)4 / benzene / 10 h / Heating

6.1: 60 percent / aq. AcOH / tetrahydrofuran / 40 h / 20 °C

7.1: 82 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 2.5 h / -78 - 0 °C

8.1: 99 percent / aq. NaClO₂; NaH₂PO₄*2H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.5 h

9.1: (PhO)2P(O)N₃; Et₃N / benzene / 3 h / Heating

10.1: 2.81 g / benzene / 24 h / Heating

11.1: 89 percent / HF*pyridine / tetrahydrofuran / 6 h / 20 °C

12.1: Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

13.1: 1.65 g / CH₂Cl₂ / 2.83 h / -78 - 0 °C

14.1: 86 percent / PPTS / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; diphenyl phosphoryl azide; pyridinium p-toluenesulfonate; Dess-Martin periodane; pyridine hydrogenfluoride; ozone; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; tert-butyl alcohol; benzene; 5.1: Suzuki reaction / 7.1: Swern oxidation / 9.1: Curtius rearrangement;
DOI:10.1039/b111146a

Reference yield:

: 13857-47-1
(E)-4-methylhept-3-en-6-yn-1-ol

: 444989-34-8
(4R)-3-[(2R,3S,5E,8E,10E,14S)-15-allyloxycarbonylamino-3-(1-ethoxyethoxy)-2,6,8,14-tetramethylpentadeca-5,8,10-trienoyl]-4-benzyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 12 steps

1.1: 99 percent / imidazole / dimethylformamide / 0.5 h / 0 °C

2.1: dichlorobis(η₅-pentadienyl)zirconium / CH2Cl2; toluene / 5.5 h / 20 °C

2.2: 88 percent / I₂ / CH₂Cl₂; toluene; tetrahydrofuran / 1 h / 0 °C

3.1: 17.86 g / aq. NaOH / Pd(PPh₃)4 / benzene / 10 h / Heating

4.1: 60 percent / aq. AcOH / tetrahydrofuran / 40 h / 20 °C

5.1: 82 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 2.5 h / -78 - 0 °C

6.1: 99 percent / aq. NaClO₂; NaH₂PO₄*2H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.5 h

7.1: (PhO)2P(O)N₃; Et₃N / benzene / 3 h / Heating

8.1: 2.81 g / benzene / 24 h / Heating

9.1: 89 percent / HF*pyridine / tetrahydrofuran / 6 h / 20 °C

10.1: Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

11.1: 1.65 g / CH₂Cl₂ / 2.83 h / -78 - 0 °C

12.1: 86 percent / PPTS / CH₂Cl₂ / 1.5 h / 20 °C

With 1H-imidazole; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; diphenyl phosphoryl azide; pyridinium p-toluenesulfonate; Dess-Martin periodane; pyridine hydrogenfluoride; acetic acid; dimethyl sulfoxide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; zirconocene dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene; 3.1: Suzuki reaction / 5.1: Swern oxidation / 7.1: Curtius rearrangement;
DOI:10.1039/b111146a