(2S,10R,10aS)-9-allyloxy-10-benzoyloxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (2'R,3'S)-3'-benzoylamino-2'-hydroxy-3'-(2-allylphenyl)-propanoate

Base Information

Chemical Name:(2S,10R,10aS)-9-allyloxy-10-benzoyloxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (2'R,3'S)-3'-benzoylamino-2'-hydroxy-3'-(2-allylphenyl)-propanoate
CAS No.:1352213-09-2
Molecular Formula:C₄₁H₄₀N₂O₇
Molecular Weight:672.778
Hs Code.:

(2S,10R,10aS)-9-allyloxy-10-benzoyloxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (2'R,3'S)-3'-benzoylamino-2'-hydroxy-3'-(2-allylphenyl)-propanoate

Synonyms:(2S,10R,10aS)-9-allyloxy-10-benzoyloxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (2'R,3'S)-3'-benzoylamino-2'-hydroxy-3'-(2-allylphenyl)-propanoate

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Chemical Property of (2S,10R,10aS)-9-allyloxy-10-benzoyloxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (2'R,3'S)-3'-benzoylamino-2'-hydroxy-3'-(2-allylphenyl)-propanoate

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Technology Process of (2S,10R,10aS)-9-allyloxy-10-benzoyloxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (2'R,3'S)-3'-benzoylamino-2'-hydroxy-3'-(2-allylphenyl)-propanoate

There total 22 articles about (2S,10R,10aS)-9-allyloxy-10-benzoyloxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (2'R,3'S)-3'-benzoylamino-2'-hydroxy-3'-(2-allylphenyl)-propanoate 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: 89.0%

: 1352213-08-1
(2S,10R,10aS)-9-allyloxy-10-benzoyloxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (2'R,3'S)-3'-benzoylamino-2'-triisopropylsilyloxy-3'-(2-allylphenyl)-propanoate

: 1352213-09-2
(2S,10R,10aS)-9-allyloxy-10-benzoyloxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (2'R,3'S)-3'-benzoylamino-2'-hydroxy-3'-(2-allylphenyl)-propanoate

Guidance literature:: With pyridine; hydrogen fluoride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1016/j.bmc.2011.10.010

Reference yield:

: 401564-17-8
(2S,4S)-1-(tert-butoxycarbonyl)-4-((tert-butyldimethylsilyl)oxy)pyrrolidine-2-carboxylic acid

: 1352213-09-2
(2S,10R,10aS)-9-allyloxy-10-benzoyloxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (2'R,3'S)-3'-benzoylamino-2'-hydroxy-3'-(2-allylphenyl)-propanoate

Guidance literature:: Multi-step reaction with 11 steps

1.1: triethylamine / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

2.1: tetrahydrofuran / 20 h / 0 °C / Inert atmosphere; Reflux

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

3.2: 0.25 h / 0 °C / Inert atmosphere

4.1: zinc dibromide / dichloromethane / 0 - 20 °C / Inert atmosphere

4.2: Inert atmosphere

5.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; hexane / 3.17 h / -78 °C / Inert atmosphere

7.1: pyridine; hydrogen fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

8.1: sodium tetrahydroborate / methanol / 1 h / 20 °C / Inert atmosphere

9.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere

9.2: 0.33 h / 0 °C / Inert atmosphere

10.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

10.2: 3 h / -78 °C / Inert atmosphere

11.1: pyridine; hydrogen fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; n-butyllithium; hydrogen fluoride; sodium tris(acetoxy)borohydride; sodium hydride; triethylamine; zinc dibromide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.bmc.2011.10.010

Reference yield:

: 1352212-84-0
3-(allyloxy)-2-iodobenzaldehyde

: 1352213-09-2
(2S,10R,10aS)-9-allyloxy-10-benzoyloxy-1,2,3,5,10,10a-hexahydropyrrolo[1,2-b]isoquinolin-2-yl (2'R,3'S)-3'-benzoylamino-2'-hydroxy-3'-(2-allylphenyl)-propanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 3.17 h / -78 °C / Inert atmosphere

3.1: pyridine; hydrogen fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

4.1: sodium tetrahydroborate / methanol / 1 h / 20 °C / Inert atmosphere

5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere

5.2: 0.33 h / 0 °C / Inert atmosphere

6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

6.2: 3 h / -78 °C / Inert atmosphere

7.1: pyridine; hydrogen fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; n-butyllithium; hydrogen fluoride; sodium tris(acetoxy)borohydride; sodium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; 1,2-dichloro-ethane; mineral oil;
DOI:10.1016/j.bmc.2011.10.010