(3R)-3-[2-[(tert-butyldimethylsilyl)oxy]ethyl]-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraene

Base Information

• Chemical Name: (3R)-3-[2-[(tert-butyldimethylsilyl)oxy]ethyl]-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraene
• CAS No.: 1388894-14-1
• Molecular Formula: C₂₇H₄₃N₃O₃SSi
• Molecular Weight: 517.808

Synonyms:(3R)-3-[2-[(tert-butyldimethylsilyl)oxy]ethyl]-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraene

Chemical Property of (3R)-3-[2-[(tert-butyldimethylsilyl)oxy]ethyl]-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (3R)-3-[2-[(tert-butyldimethylsilyl)oxy]ethyl]-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraene

There total 6 articles about (3R)-3-[2-[(tert-butyldimethylsilyl)oxy]ethyl]-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽¹²⁾,2⁽⁶⁾,8,10-tetraene 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: 63.0%

(1r,4r)-4-(morpholin-4-yl)cyclohexan-1-ol (1228947-14-5) + (3R)-3-[2-[(tert-butyldimethylsilyl)oxy]ethyl]-12-chloro-7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1(8),2(6),9,11-tetraene (1388894-05-0) → (3R)-3-[2-[(tert-butyldimethylsilyl)oxy]ethyl]-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1(12),2(6),8,10-tetraene (1388894-14-1)

Guidance literature:

(1r,4r)-4-(morpholin-4-yl)cyclohexan-1-ol; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

(3R)-3-[2-[(tert-butyldimethylsilyl)oxy]ethyl]-12-chloro-7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraene; In tetrahydrofuran; mineral oil; at 60 ℃; for 3h; Inert atmosphere;

Reference yield:

ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate (1029689-54-0) → (3R)-3-[2-[(tert-butyldimethylsilyl)oxy]ethyl]-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1(12),2(6),8,10-tetraene (1388894-14-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 20 - 180 °C / Inert atmosphere

1.2: Cooling with ice

2.1: trichlorophosphate / 20 - 110 °C

3.1: diisobutylaluminium hydride / hexane; tetrahydrofuran / -30 °C / Inert atmosphere

4.1: CHIRALPAK IA / carbon dioxide; methanol / Resolution of racemate

5.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

6.2: 3 h / 60 °C / Inert atmosphere

With 1H-imidazole; sodium hydride; diisobutylaluminium hydride; trichlorophosphate; In tetrahydrofuran; methanol; hexane; carbon dioxide; N,N-dimethyl-formamide; mineral oil;

Reference yield:

ethyl 2-[12-hydroxy-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]acetate (1388893-76-2) → (3R)-3-[2-[(tert-butyldimethylsilyl)oxy]ethyl]-12-[[4-(morpholin-4-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1(12),2(6),8,10-tetraene (1388894-14-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: trichlorophosphate / 20 - 110 °C

2.1: diisobutylaluminium hydride / hexane; tetrahydrofuran / -30 °C / Inert atmosphere

3.1: CHIRALPAK IA / carbon dioxide; methanol / Resolution of racemate

4.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

5.2: 3 h / 60 °C / Inert atmosphere

With 1H-imidazole; sodium hydride; diisobutylaluminium hydride; trichlorophosphate; In tetrahydrofuran; methanol; hexane; carbon dioxide; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate

(1r,4r)-4-(morpholin-4-yl)cyclohexan-1-ol

(3R)-3-[2-[(tert-butyldimethylsilyl)oxy]ethyl]-12-chloro-7-thia-9,11-diazatricyclo[6.4.0.0(2,6)]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraene

ethyl 2-[12-hydroxy-7-thia-9,11-diazatricyclo[6.4.0.0[2.6]]dodeca-1⁽⁸⁾,2⁽⁶⁾,9,11-tetraen-3-yl]acetate

Downstream raw materials:

C₂₁H₂₉N₃O₃S

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