(6R,10R)-(+)-5-benzyl-9-<(tert-butyldimethylsilyl)oxy>-12-(prop-2-ynyl)-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole

Base Information

• Chemical Name: (6R,10R)-(+)-5-benzyl-9-<(tert-butyldimethylsilyl)oxy>-12-(prop-2-ynyl)-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole
• CAS No.: 129708-77-6
• Molecular Formula: C₃₀H₃₆N₂OSi
• Molecular Weight: 468.714

Synonyms:(6R,10R)-(+)-5-benzyl-9-<(tert-butyldimethylsilyl)oxy>-12-(prop-2-ynyl)-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole

Chemical Property of (6R,10R)-(+)-5-benzyl-9-<(tert-butyldimethylsilyl)oxy>-12-(prop-2-ynyl)-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,10R)-(+)-5-benzyl-9-<(tert-butyldimethylsilyl)oxy>-12-(prop-2-ynyl)-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole

There total 9 articles about (6R,10R)-(+)-5-benzyl-9-<(tert-butyldimethylsilyl)oxy>-12-(prop-2-ynyl)-6,7,10,11-tetrahydro-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: 82.0%

t-butyldimethylsiyl triflate (69739-34-0) + (6R,10R)-(+)-5-benzyl-9-oxo-12-(prop-2-ynyl)-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole (119184-26-8) → (6R,10R)-(+)-5-benzyl-9-<(tert-butyldimethylsilyl)oxy>-12-(prop-2-ynyl)-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole (129708-77-6)

Guidance literature:

With triethylamine; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1021/ja00169a033

Reference yield:

(S)-3-(1-Benzyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester (129708-73-2) → (6R,10R)-(+)-5-benzyl-9-<(tert-butyldimethylsilyl)oxy>-12-(prop-2-ynyl)-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole (129708-77-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / sodium borohydride / methanol / 1 h / 25 °C

2: 67 percent / benzene; dioxane / 24 h / Heating

3: chlorotrimethylsilane / 25 °C

4: 72 percent / NaH, MeOH / toluene / 16 h / Heating

5: 99 percent / HOAc, H₂SO₄ / H₂O / 72 h / Heating

6: 85 percent / 88percent aq. formic acid / 10percent Pd/C / 2 h / Ambient temperature

7: 60 percent / K₂CO₃ / ethanol; toluene / 12 h / Ambient temperature

8: 82 percent / Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

With methanol; sodium tetrahydroborate; chloro-trimethyl-silane; formic acid; sulfuric acid; sodium hydride; potassium carbonate; acetic acid; triethylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane; water; toluene; benzene;

DOI:10.1021/ja00169a033

Reference yield:

(6R,10R)-(+)-5,12-dibenzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole (129708-76-5) → (6R,10R)-(+)-5-benzyl-9-<(tert-butyldimethylsilyl)oxy>-12-(prop-2-ynyl)-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole (129708-77-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / 88percent aq. formic acid / 10percent Pd/C / 2 h / Ambient temperature

2: 60 percent / K₂CO₃ / ethanol; toluene / 12 h / Ambient temperature

3: 82 percent / Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

With formic acid; potassium carbonate; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; toluene;

DOI:10.1021/ja00169a033

upstream raw materials:

t-butyldimethylsiyl triflate

(6R,10R)-(+)-5-benzyl-9-oxo-12-(prop-2-ynyl)-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

(S)-3-(1-Benzyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester

(6R,10R)-(+)-5,12-dibenzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole

Downstream raw materials:

(6R,10R)-(+)-methyl 5-benzyl-9-<(tert-butyldimethylsilyl)oxy>-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole-12-but-2-ynoate

(E)-(+)-(16S)-12-benzyl-10-desoxy-18-oxo-18-methoxysarpagine

(Z)-(+)-(16S)-12-benzyl-10-desoxy-18-oxo-18-methoxysarpagine

(E)-(+)-(16S)-12-benzyl-10-desoxy-18-hydroxysarpagine

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