(3S,12bR)-3-((2S,3S)-5-(tert-butyldimethylsilyloxy)-3-methoxy-2-(4-methoxybenzyloxy)pentyl)-10-methoxy-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one

Base Information

Chemical Name:(3S,12bR)-3-((2S,3S)-5-(tert-butyldimethylsilyloxy)-3-methoxy-2-(4-methoxybenzyloxy)pentyl)-10-methoxy-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one
CAS No.:1421052-29-0
Molecular Formula:C₄₃H₅₈N₂O₈SSi
Molecular Weight:791.094
Hs Code.:

(3S,12bR)-3-((2S,3S)-5-(tert-butyldimethylsilyloxy)-3-methoxy-2-(4-methoxybenzyloxy)pentyl)-10-methoxy-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one

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Chemical Property of (3S,12bR)-3-((2S,3S)-5-(tert-butyldimethylsilyloxy)-3-methoxy-2-(4-methoxybenzyloxy)pentyl)-10-methoxy-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one

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Technology Process of (3S,12bR)-3-((2S,3S)-5-(tert-butyldimethylsilyloxy)-3-methoxy-2-(4-methoxybenzyloxy)pentyl)-10-methoxy-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one

There total 8 articles about (3S,12bR)-3-((2S,3S)-5-(tert-butyldimethylsilyloxy)-3-methoxy-2-(4-methoxybenzyloxy)pentyl)-10-methoxy-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-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:

: 1421052-25-6
8-methoxy-9-tosyl-3,4-dihydro-β-carboline

: 1421052-24-5
(5S,6S)-8-(tert-butyldimethylsilyloxy)-6-methoxy-5-(4-methoxybenzyloxy)-3-methyleneoctan-2-one

: 1421052-29-0
(3S,12bR)-3-((2S,3S)-5-(tert-butyldimethylsilyloxy)-3-methoxy-2-(4-methoxybenzyloxy)pentyl)-10-methoxy-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one

: 1421052-26-7
(3S,12bS)-3-((2S,3S)-5-(tert-butyldimethylsilyloxy)-3-methoxy-2-(4-methoxybenzyloxy)pentyl)-10-methoxy-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one

: 1421052-27-8
(3R,12bR)-3-((2S,3S)-5-(tert-butyldimethylsilyloxy)-3-methoxy-2-(4-methoxybenzyloxy)pentyl)-10-methoxy-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one

Guidance literature:: With C₁₇H₃₄N₄OS; acetic acid; In toluene; at 23 ℃; for 144h; Inert atmosphere;
DOI:10.1021/ol400046n

Reference yield:

: (S)-4-(tert-butyldimethylsilyloxy)-2-methoxybutan-1-ol

: 1421052-29-0
(3S,12bR)-3-((2S,3S)-5-(tert-butyldimethylsilyloxy)-3-methoxy-2-(4-methoxybenzyloxy)pentyl)-10-methoxy-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -60 °C

1.2: -60 - 20 °C

2.1: titanium(IV) trichloride isopropoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere

2.2: -78 °C / Inert atmosphere

3.1: trifluorormethanesulfonic acid / diethyl ether / 1.75 h / -20 - 20 °C

4.1: tert.-butyl lithium / diethyl ether; pentane / 0.58 h / -78 °C / Inert atmosphere

4.2: 1.5 h / -78 °C / Inert atmosphere

5.1: acetic acid; C₁₇H₃₄N₄OS / toluene / 144 h / 23 °C / Inert atmosphere

With oxalyl dichloride; titanium(IV) trichloride isopropoxide; trifluorormethanesulfonic acid; C₁₇H₃₄N₄OS; tert.-butyl lithium; acetic acid; dimethyl sulfoxide; In diethyl ether; dichloromethane; toluene; pentane; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation;
DOI:10.1021/ol400046n

Reference yield:

: 1421052-20-1
(S)-(4-(benzyloxy)-3-methoxybutoxy)(tert-butyl)dimethylsilane

: 1421052-29-0
(3S,12bR)-3-((2S,3S)-5-(tert-butyldimethylsilyloxy)-3-methoxy-2-(4-methoxybenzyloxy)pentyl)-10-methoxy-12-tosyl-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 9 h / 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -60 °C

2.2: -60 - 20 °C

3.1: titanium(IV) trichloride isopropoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere

3.2: -78 °C / Inert atmosphere

4.1: trifluorormethanesulfonic acid / diethyl ether / 1.75 h / -20 - 20 °C

5.1: tert.-butyl lithium / diethyl ether; pentane / 0.58 h / -78 °C / Inert atmosphere

5.2: 1.5 h / -78 °C / Inert atmosphere

6.1: acetic acid; C₁₇H₃₄N₄OS / toluene / 144 h / 23 °C / Inert atmosphere

With oxalyl dichloride; titanium(IV) trichloride isopropoxide; trifluorormethanesulfonic acid; palladium 10% on activated carbon; C₁₇H₃₄N₄OS; hydrogen; tert.-butyl lithium; acetic acid; dimethyl sulfoxide; In diethyl ether; dichloromethane; ethyl acetate; toluene; pentane; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation;
DOI:10.1021/ol400046n