(1aS,3R,3aS,7aR,7bR)-3-Hydroxy-6-(4-methoxy-phenyl)-7a-[(Z)-(S)-1-(2-trimethylsilanyl-ethanesulfonyl)-1,2,5,6,7,8-hexahydro-azocin-2-ylmethyl]-octahydro-1-oxa-6-aza-cyclopropa[a]naphthalen-7-one

Base Information

Chemical Name:(1aS,3R,3aS,7aR,7bR)-3-Hydroxy-6-(4-methoxy-phenyl)-7a-[(Z)-(S)-1-(2-trimethylsilanyl-ethanesulfonyl)-1,2,5,6,7,8-hexahydro-azocin-2-ylmethyl]-octahydro-1-oxa-6-aza-cyclopropa[a]naphthalen-7-one
CAS No.:145387-88-8
Molecular Formula:C₂₉H₄₄N₂O₆SSi
Molecular Weight:576.83
Hs Code.:

(1aS,3R,3aS,7aR,7bR)-3-Hydroxy-6-(4-methoxy-phenyl)-7a-[(Z)-(S)-1-(2-trimethylsilanyl-ethanesulfonyl)-1,2,5,6,7,8-hexahydro-azocin-2-ylmethyl]-octahydro-1-oxa-6-aza-cyclopropa[a]naphthalen-7-one

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Chemical Property of (1aS,3R,3aS,7aR,7bR)-3-Hydroxy-6-(4-methoxy-phenyl)-7a-[(Z)-(S)-1-(2-trimethylsilanyl-ethanesulfonyl)-1,2,5,6,7,8-hexahydro-azocin-2-ylmethyl]-octahydro-1-oxa-6-aza-cyclopropa[a]naphthalen-7-one

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Technology Process of (1aS,3R,3aS,7aR,7bR)-3-Hydroxy-6-(4-methoxy-phenyl)-7a-[(Z)-(S)-1-(2-trimethylsilanyl-ethanesulfonyl)-1,2,5,6,7,8-hexahydro-azocin-2-ylmethyl]-octahydro-1-oxa-6-aza-cyclopropa[a]naphthalen-7-one

There total 15 articles about (1aS,3R,3aS,7aR,7bR)-3-Hydroxy-6-(4-methoxy-phenyl)-7a-[(Z)-(S)-1-(2-trimethylsilanyl-ethanesulfonyl)-1,2,5,6,7,8-hexahydro-azocin-2-ylmethyl]-octahydro-1-oxa-6-aza-cyclopropa[a]naphthalen-7-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:

: 124981-58-4
1-(2-Methoxy-ethyl)-cyclohexa-2,5-dienecarboxylic acid

: 145387-88-8
(1aS,3R,3aS,7aR,7bR)-3-Hydroxy-6-(4-methoxy-phenyl)-7a-[(Z)-(S)-1-(2-trimethylsilanyl-ethanesulfonyl)-1,2,5,6,7,8-hexahydro-azocin-2-ylmethyl]-octahydro-1-oxa-6-aza-cyclopropa[a]naphthalen-7-one

Guidance literature:: Multi-step reaction with 15 steps

1: 1) (PhO)2P(=O)N₃, Et₃N, pyrrolidine; 2) I₂, H₂O / 2) THF

2: 2,2'-azobisisobutyronitrile / benzene / Ambient temperature

4: 4-(N,N-dimethylamino)pyridine, pyridine

6: BBr₃

7: Swern oxidation

9: 68 percent / H₂, pyridine / BaSO₄

10: 86 percent / Ph₃P, diethyl azodicarboxylate

11: (CH₃)3SiCl, NaI / acetonitrile

12: Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂

13: 91 percent / KH, 18-crown-6, tetra-n-butylammonium iodide

14: LiOH

15: VO(acac)2, t-BuOOH / Heating

With pyrrolidine; pyridine; tert.-butylhydroperoxide; dmap; lithium hydroxide; chloro-trimethyl-silane; bis(acetylacetonate)oxovanadium; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); diphenyl phosphoryl azide; water; hydrogen; iodine; boron tribromide; tetra-(n-butyl)ammonium iodide; potassium hydride; triethylamine; triphenylphosphine; sodium iodide; diethylazodicarboxylate; barium sulfate; In dichloromethane; acetonitrile; benzene;
DOI:10.1016/S0040-4039(00)60944-9

Reference yield:

: 145387-74-2
(1R,5R,8R)-8-Iodo-1-(2-methoxy-ethyl)-6-oxa-bicyclo[3.2.1]oct-2-en-7-one

: 145387-88-8
(1aS,3R,3aS,7aR,7bR)-3-Hydroxy-6-(4-methoxy-phenyl)-7a-[(Z)-(S)-1-(2-trimethylsilanyl-ethanesulfonyl)-1,2,5,6,7,8-hexahydro-azocin-2-ylmethyl]-octahydro-1-oxa-6-aza-cyclopropa[a]naphthalen-7-one

Guidance literature:: Multi-step reaction with 14 steps

1: 2,2'-azobisisobutyronitrile / benzene / Ambient temperature

3: 4-(N,N-dimethylamino)pyridine, pyridine

5: BBr₃

6: Swern oxidation

8: 68 percent / H₂, pyridine / BaSO₄

9: 86 percent / Ph₃P, diethyl azodicarboxylate

10: (CH₃)3SiCl, NaI / acetonitrile

11: Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂

12: 91 percent / KH, 18-crown-6, tetra-n-butylammonium iodide

13: LiOH

14: VO(acac)2, t-BuOOH / Heating

With pyridine; tert.-butylhydroperoxide; dmap; lithium hydroxide; chloro-trimethyl-silane; bis(acetylacetonate)oxovanadium; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); hydrogen; boron tribromide; tetra-(n-butyl)ammonium iodide; potassium hydride; triethylamine; triphenylphosphine; sodium iodide; diethylazodicarboxylate; barium sulfate; In dichloromethane; acetonitrile; benzene;
DOI:10.1016/S0040-4039(00)60944-9

Reference yield:

: (1S,5R,6S)-6-Allyl-5-hydroxy-1-(2-methoxy-ethyl)-cyclohex-2-enecarboxylic acid (4-methoxy-phenyl)-amide

: 145387-88-8
(1aS,3R,3aS,7aR,7bR)-3-Hydroxy-6-(4-methoxy-phenyl)-7a-[(Z)-(S)-1-(2-trimethylsilanyl-ethanesulfonyl)-1,2,5,6,7,8-hexahydro-azocin-2-ylmethyl]-octahydro-1-oxa-6-aza-cyclopropa[a]naphthalen-7-one

Guidance literature:: Multi-step reaction with 12 steps

1: 4-(N,N-dimethylamino)pyridine, pyridine

3: BBr₃

4: Swern oxidation

6: 68 percent / H₂, pyridine / BaSO₄

7: 86 percent / Ph₃P, diethyl azodicarboxylate

8: (CH₃)3SiCl, NaI / acetonitrile

9: Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂

10: 91 percent / KH, 18-crown-6, tetra-n-butylammonium iodide

11: LiOH

12: VO(acac)2, t-BuOOH / Heating

With pyridine; tert.-butylhydroperoxide; dmap; lithium hydroxide; chloro-trimethyl-silane; bis(acetylacetonate)oxovanadium; 18-crown-6 ether; hydrogen; boron tribromide; tetra-(n-butyl)ammonium iodide; potassium hydride; triethylamine; triphenylphosphine; sodium iodide; diethylazodicarboxylate; barium sulfate; In dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(00)60944-9