(-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-hydroxyethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

Base Information

• Chemical Name: (-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-hydroxyethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole
• CAS No.: 143065-04-7
• Molecular Formula: C₂₉H₃₆N₂O₃
• Molecular Weight: 460.616

Synonyms:(-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-hydroxyethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

Chemical Property of (-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-hydroxyethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-hydroxyethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

There total 10 articles about (-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-hydroxyethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole 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: 99.0%

(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-oxomethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]-indole (143065-03-6) → (-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-hydroxyethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole (143065-04-7)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃; for 1h;

DOI:10.1021/jo00055a019

Reference yield:

(6S,10S)-(-)-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole (123806-87-1) → (-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-hydroxyethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole (143065-04-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) LDA, KOH, 2.) LiClO4, n-Bu3PO / 2.) toluene, Δ

2: Mg / tetrahydrofuran / 0 °C

3: KH, 18-crown-6 / dioxane; various solvent(s) / 150 °C

4: 90 percent / pTSA / benzene / Heating

5: 90 percent / OsO₄, pyridine, NaHSO₃, NaIO₄ / tetrahydrofuran; methanol / 0 °C

6: 95 percent / NaBH₄ / ethanol

With pyridine; potassium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; 18-crown-6 ether; Tributylphosphine oxide; lithium perchlorate; potassium hydride; toluene-4-sulfonic acid; sodium hydrogensulfite; magnesium; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; benzene;

DOI:10.1021/ja00043a043

Reference yield:

(6S,10S,8E)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-6,10-epimino-5H-cyclooctindole-9-carbaldehyde (143120-74-5) → (-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-hydroxyethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole (143065-04-7)

Guidance literature:

Multi-step reaction with 5 steps

1: Mg / tetrahydrofuran / 0 °C

2: KH, 18-crown-6 / dioxane; various solvent(s) / 150 °C

3: 90 percent / pTSA / benzene / Heating

4: 90 percent / OsO₄, pyridine, NaHSO₃, NaIO₄ / tetrahydrofuran; methanol / 0 °C

5: 95 percent / NaBH₄ / ethanol

With pyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; 18-crown-6 ether; potassium hydride; toluene-4-sulfonic acid; sodium hydrogensulfite; magnesium; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; benzene;

DOI:10.1021/ja00043a043

upstream raw materials:

(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-oxomethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]-indole

(-)-(6S,10S)-5-methyl-9-(2'-ethyl-1'-hydroxy-3'-hexenyl)-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooct[b]indole

(-)-(6S,10S)-5-methyl-8-(1'-ethyl-2'-pentenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole-9-carboxaldehyde

(-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-pentenyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

Downstream raw materials:

(-)-N_b-benzylraumacline

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