Technology Process of (1R,3S,4S,7R,8R,11R,12S,13R)-4,12,13-Tris-benzyloxy-8-(4-methoxy-phenyl)-2,9,14-trioxa-6-aza-tricyclo[9.2.1.03,7]tetradecane-6-carboxylic acid benzyl ester
There total 34 articles about (1R,3S,4S,7R,8R,11R,12S,13R)-4,12,13-Tris-benzyloxy-8-(4-methoxy-phenyl)-2,9,14-trioxa-6-aza-tricyclo[9.2.1.03,7]tetradecane-6-carboxylic acid benzyl ester 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:
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![(1R,3S,4S,7R,8R,11R,12S,13R)-4,12,13-Tris-benzyloxy-8-(4-methoxy-phenyl)-2,9,14-trioxa-6-aza-tricyclo[9.2.1.0<sup>3,7</sup>]tetradecane-6-carboxylic acid benzyl ester](/Databaselist/images/loading.webp)
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164217-36-1
(1R,3S,4S,7R,8R,11R,12S,13R)-4,12,13-Tris-benzyloxy-8-(4-methoxy-phenyl)-2,9,14-trioxa-6-aza-tricyclo[9.2.1.03,7]tetradecane-6-carboxylic acid benzyl ester
- Guidance literature:
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With
N-Bromosuccinimide; 4 A molecular sieve;
In
toluene;
at 90 ℃;
for 20h;
DOI:10.1016/S0040-4039(00)76839-0
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164217-36-1
(1R,3S,4S,7R,8R,11R,12S,13R)-4,12,13-Tris-benzyloxy-8-(4-methoxy-phenyl)-2,9,14-trioxa-6-aza-tricyclo[9.2.1.03,7]tetradecane-6-carboxylic acid benzyl ester
- Guidance literature:
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Multi-step reaction with 6 steps
1: K2CO3 / tetrahydrofuran; H2O / 0.5 h / 25 °C
2: dl-10-camphorosulfonic acid / CH2Cl2 / 0.5 h / 25 °C
3: 91 percent / DIBAL / toluene / 0.5 h / -78 °C
4: 1.) n-BuLi, MS 4A / 1.) DMF, hexane, 0 deg C, 5 min, 2.) DMF, 25 deg C, 0.5 h
5: 90 percent / dl-10-camphorosulfonic acid / methanol; dioxane / 2 h / 25 °C
6: 64 percent / NBS, MS4AP / toluene / 24 h / 90 °C / var. solvents, temp., times
With
N-Bromosuccinimide; n-butyllithium; DL-10-camphorsulfonic acid; diisobutylaluminium hydride; potassium carbonate;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; toluene;
DOI:10.1246/bcsj.67.3057
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164217-36-1
(1R,3S,4S,7R,8R,11R,12S,13R)-4,12,13-Tris-benzyloxy-8-(4-methoxy-phenyl)-2,9,14-trioxa-6-aza-tricyclo[9.2.1.03,7]tetradecane-6-carboxylic acid benzyl ester
- Guidance literature:
-
Multi-step reaction with 7 steps
1: imidazole / dimethylformamide / 0.5 h / 25 °C
2: tetrabutylammonium iodide, NaH / tetrahydrofuran / 2 h / 25 °C
3: (n-Bu4)NF / tetrahydrofuran / 0.5 h / 25 °C
4: triethylamine / CH2Cl2 / 0.08 h / -78 °C
5: 1.) n-BuLi, MS 4A / 1.) DMF, hexane, 0 deg C, 5 min, 2.) DMF, 25 deg C, 0.5 h
6: 90 percent / dl-10-camphorosulfonic acid / methanol; dioxane / 2 h / 25 °C
7: 64 percent / NBS, MS4AP / toluene / 24 h / 90 °C / var. solvents, temp., times
With
1H-imidazole; N-Bromosuccinimide; n-butyllithium; DL-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1246/bcsj.67.3057
