(8S,8aS)-6-[(E)-(2S,6S)-6-Benzyloxy-1-iodo-2,5-dimethyl-oct-4-en-(E)-ylidene]-8-methyl-octahydro-indolizin-8-ol

Base Information

• Chemical Name: (8S,8aS)-6-[(E)-(2S,6S)-6-Benzyloxy-1-iodo-2,5-dimethyl-oct-4-en-(E)-ylidene]-8-methyl-octahydro-indolizin-8-ol
• CAS No.: 116505-81-8
• Molecular Formula: C₂₆H₃₈INO₂
• Molecular Weight: 523.498

Synonyms:(8S,8aS)-6-[(E)-(2S,6S)-6-Benzyloxy-1-iodo-2,5-dimethyl-oct-4-en-(E)-ylidene]-8-methyl-octahydro-indolizin-8-ol

Chemical Property of (8S,8aS)-6-[(E)-(2S,6S)-6-Benzyloxy-1-iodo-2,5-dimethyl-oct-4-en-(E)-ylidene]-8-methyl-octahydro-indolizin-8-ol

Chemical Property:

Purity/Quality:

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Technology Process of (8S,8aS)-6-[(E)-(2S,6S)-6-Benzyloxy-1-iodo-2,5-dimethyl-oct-4-en-(E)-ylidene]-8-methyl-octahydro-indolizin-8-ol

There total 14 articles about (8S,8aS)-6-[(E)-(2S,6S)-6-Benzyloxy-1-iodo-2,5-dimethyl-oct-4-en-(E)-ylidene]-8-methyl-octahydro-indolizin-8-ol 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: 14.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (E)-(2S,10S)-10-Benzyloxy-6,9-dimethyl-2-(S)-pyrrolidin-2-yl-dodec-8-en-4-yn-2-ol → (8S,8aS)-8-hydroxy-8-methyl-(6E)-<(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-1-iodo-4-octenylidene>octahydroindolizine (116561-36-5) + (8S,8aS)-6-[(E)-(2S,6S)-6-Benzyloxy-1-iodo-2,5-dimethyl-oct-4-en-(E)-ylidene]-8-methyl-octahydro-indolizin-8-ol (116505-81-8)

Guidance literature:

With camphor-10-sulfonic acid; sodium iodide; at 100 ℃; for 1h;

DOI:10.1021/ja961641q

Reference yield:

benzyl bromide (100-39-0) → (8S,8aS)-6-[(E)-(2S,6S)-6-Benzyloxy-1-iodo-2,5-dimethyl-oct-4-en-(E)-ylidene]-8-methyl-octahydro-indolizin-8-ol (116505-81-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) NaH, 2.) Me₄NCl / 1.) THF, RT, 1 h, 2.) THF, RT, 17 h

2: 84 percent / O₃ / methanol / 2 h / -78 °C

3: 2.) EtCOCl, HMPA / 1.) THF, 3 h, 2.) THF, RT, overnight

4: 1.) LDA, HMPA / 1.) THF, hexane, 0 deg C, 15 min, 2.) THF, hexane, RT, 4.5 h

5: 90 percent / aq. HCl / Ambient temperature

6: 1.) LiAlH₄, 2.) aq. NaOH / 1.) Et₂O, 0 deg C, 1 h, 2.) Et₂O, RT, 1 h

7: 90 percent / Et₃N, Py*SO₃ / dimethylsulfoxide / 1 h / Ambient temperature

8: 1.) Ph₃P, K₂CO₃ / 1.) CH₂Cl₂, RT, 30 min, 2.) CH₂Cl₂, RT, 45 min

9: 96 percent / nBuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C

10: 1.) nBuLi, 2.) Et₂AlCl

11: 71 percent / Ba(OH)2*8H₂O / 1,2-dimethoxy-ethane / Heating

12: 14 percent / aq. NaI, camphorsulfonic acid / 1 h / 100 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; barium dihydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; camphor-10-sulfonic acid; diethylaluminium chloride; sulfur trioxide pyridine complex; propionyl chloride; tetramethlyammonium chloride; sodium hydride; potassium carbonate; ozone; triethylamine; triphenylphosphine; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dimethyl sulfoxide;

DOI:10.1021/ja961641q

Reference yield:

(S)-(-)-2-methyl-1-penten-3-ol (98168-21-9,2088-07-5) → (8S,8aS)-6-[(E)-(2S,6S)-6-Benzyloxy-1-iodo-2,5-dimethyl-oct-4-en-(E)-ylidene]-8-methyl-octahydro-indolizin-8-ol (116505-81-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) NaH, 2.) Me₄NCl / 1.) THF, RT, 1 h, 2.) THF, RT, 17 h

2: 84 percent / O₃ / methanol / 2 h / -78 °C

3: 2.) EtCOCl, HMPA / 1.) THF, 3 h, 2.) THF, RT, overnight

4: 1.) LDA, HMPA / 1.) THF, hexane, 0 deg C, 15 min, 2.) THF, hexane, RT, 4.5 h

5: 90 percent / aq. HCl / Ambient temperature

6: 1.) LiAlH₄, 2.) aq. NaOH / 1.) Et₂O, 0 deg C, 1 h, 2.) Et₂O, RT, 1 h

7: 90 percent / Et₃N, Py*SO₃ / dimethylsulfoxide / 1 h / Ambient temperature

8: 1.) Ph₃P, K₂CO₃ / 1.) CH₂Cl₂, RT, 30 min, 2.) CH₂Cl₂, RT, 45 min

9: 96 percent / nBuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C

10: 1.) nBuLi, 2.) Et₂AlCl

11: 71 percent / Ba(OH)2*8H₂O / 1,2-dimethoxy-ethane / Heating

12: 14 percent / aq. NaI, camphorsulfonic acid / 1 h / 100 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; barium dihydroxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; camphor-10-sulfonic acid; diethylaluminium chloride; sulfur trioxide pyridine complex; propionyl chloride; tetramethlyammonium chloride; sodium hydride; potassium carbonate; ozone; triethylamine; triphenylphosphine; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dimethyl sulfoxide;

DOI:10.1021/ja961641q

upstream raw materials:

((E)-(1S,5S)-1-Ethyl-2,5-dimethyl-hept-2-en-6-ynyloxymethyl)-benzene

formaldehyd

benzyl bromide

(S)-(-)-2-methyl-1-penten-3-ol

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