ethyl (1S,5S,4R,6R)-12-aza-5-methyl-7-oxo-4-(phenylmethoxy)tetracyclo[10.4.0<1,6>.0<3,8>]hexadecane-8-carboxylate

Base Information

Chemical Name:ethyl (1S,5S,4R,6R)-12-aza-5-methyl-7-oxo-4-(phenylmethoxy)tetracyclo[10.4.0<1,6>.0<3,8>]hexadecane-8-carboxylate
CAS No.:869385-01-3
Molecular Formula:C₂₆H₃₅NO₄
Molecular Weight:425.568
Hs Code.:

Synonyms:ethyl (1S,5S,4R,6R)-12-aza-5-methyl-7-oxo-4-(phenylmethoxy)tetracyclo[10.4.0<1,6>.0<3,8>]hexadecane-8-carboxylate

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Chemical Property of ethyl (1S,5S,4R,6R)-12-aza-5-methyl-7-oxo-4-(phenylmethoxy)tetracyclo[10.4.0<1,6>.0<3,8>]hexadecane-8-carboxylate

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Technology Process of ethyl (1S,5S,4R,6R)-12-aza-5-methyl-7-oxo-4-(phenylmethoxy)tetracyclo[10.4.0<1,6>.0<3,8>]hexadecane-8-carboxylate

There total 26 articles about ethyl (1S,5S,4R,6R)-12-aza-5-methyl-7-oxo-4-(phenylmethoxy)tetracyclo[10.4.0<1,6>.0<3,8>]hexadecane-8-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: 81.0%

: (9R,12S,13R,E)-ethyl 13-benzyloxy-12-methyl-10-oxo-3,4,6,7,8,9,10,11,12,13-decahydro-2H-pyrido[1,2-a][1]azacyclododecine-9-carboxylate

: 869385-01-3
ethyl (1S,5S,4R,6R)-12-aza-5-methyl-7-oxo-4-(phenylmethoxy)tetracyclo[10.4.0<1,6>.0<3,8>]hexadecane-8-carboxylate

Guidance literature:: With piperdinium acetate; In ethanol; at 80 ℃; for 48h;
DOI:10.1002/anie.200502296

Reference yield:

: 869385-17-1
methyl 5-(allyl(tert-butoxycarbonyl)amino)pentanoate

: 869385-01-3
ethyl (1S,5S,4R,6R)-12-aza-5-methyl-7-oxo-4-(phenylmethoxy)tetracyclo[10.4.0<1,6>.0<3,8>]hexadecane-8-carboxylate

Guidance literature:: Multi-step reaction with 17 steps

1: tetrahydrofuran / 2 h / 0 - 20 °C

2: aq. H₂O₂; NaOH / tetrahydrofuran / cooling

3: 13.8 g / imidazole / dimethylformamide / 3 h / 20 °C

4: 98 percent / n-BuLi / tetrahydrofuran / 10 h / -78 - 10 °C

5: 3.04 g / NaH / tetrahydrofuran / 2 h / -78 - -20 °C

6: L-selectride / tetrahydrofuran / 1.5 h / -78 °C

7: 9.22 g / imidazole / dimethylformamide / 18 h

8: 87 percent / Dibal-H / CH₂Cl₂ / 6.25 h / -78 - -50 °C

9: 82 percent / SnCl₂ / CH₂Cl₂ / 0.33 h / 20 °C

10: 72 percent / HF*pyr / tetrahydrofuran / 7 h / 0 °C

11: I₂; PPh₃; imidazole / CH₂Cl₂ / 2.5 h / -5 °C

12: 566 mg / Cs₂CO₃ / tetrahydrofuran / 40 h / 37 °C

13: HF*pyridine / tetrahydrofuran / 12 h / 20 °C

14: 180 mg / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

15: 97 percent / Me₂S; TFA / CH₂Cl₂ / 20 h / 0 - 20 °C

16: ZnCl₂

17: SiO₂

With 1H-imidazole; sodium hydroxide; n-butyllithium; dimethylsulfide; dihydrogen peroxide; iodine; silica gel; L-Selectride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; caesium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; triphenylphosphine; trifluoroacetic acid; tin(ll) chloride; zinc(II) chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 5: Horner-Wadsworth-Emmons reaction / 14: Dess-Martin oxidation / 16: Michael addition / 17: Mannich cyclization;
DOI:10.1002/anie.200502296

Reference yield:

: 869384-94-1
(3S,4R,E)-4-(benzyloxy)-3-methyl-6-phenylhex-5-enenitrile

: 869385-01-3
ethyl (1S,5S,4R,6R)-12-aza-5-methyl-7-oxo-4-(phenylmethoxy)tetracyclo[10.4.0<1,6>.0<3,8>]hexadecane-8-carboxylate

Guidance literature:: Multi-step reaction with 14 steps

1.1: O₃ / methanol; CH₂Cl₂ / -78 °C

1.2: Me₂S / methanol; CH₂Cl₂ / 3 h / 20 °C

2.1: 3.04 g / NaH / tetrahydrofuran / 2 h / -78 - -20 °C

3.1: L-selectride / tetrahydrofuran / 1.5 h / -78 °C

4.1: 9.22 g / imidazole / dimethylformamide / 18 h

5.1: 87 percent / Dibal-H / CH₂Cl₂ / 6.25 h / -78 - -50 °C

6.1: 82 percent / SnCl₂ / CH₂Cl₂ / 0.33 h / 20 °C

7.1: 72 percent / HF*pyr / tetrahydrofuran / 7 h / 0 °C

8.1: I₂; PPh₃; imidazole / CH₂Cl₂ / 2.5 h / -5 °C

9.1: 566 mg / Cs₂CO₃ / tetrahydrofuran / 40 h / 37 °C

10.1: HF*pyridine / tetrahydrofuran / 12 h / 20 °C

11.1: 180 mg / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

12.1: 97 percent / Me₂S; TFA / CH₂Cl₂ / 20 h / 0 - 20 °C

13.1: ZnCl₂

14.1: SiO₂

With 1H-imidazole; dimethylsulfide; iodine; silica gel; L-Selectride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; caesium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; ozone; triphenylphosphine; trifluoroacetic acid; tin(ll) chloride; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 2.1: Horner-Wadsworth-Emmons reaction / 11.1: Dess-Martin oxidation / 13.1: Michael addition / 14.1: Mannich cyclization;
DOI:10.1002/anie.200502296