(4R,4aR,6S,7S,8aS)-2-(tert-butoxycarbonyl)-4-[3-(1,3-dioxolan-2-yl)propyl]-7-hydroxy-6,4-(iminomethano)-9-(p-toluenesulfonyl)perhydroisoquinoline

Base Information

Chemical Name:(4R,4aR,6S,7S,8aS)-2-(tert-butoxycarbonyl)-4-[3-(1,3-dioxolan-2-yl)propyl]-7-hydroxy-6,4-(iminomethano)-9-(p-toluenesulfonyl)perhydroisoquinoline
CAS No.:1428872-52-9
Molecular Formula:C₂₈H₄₂N₂O₇S
Molecular Weight:550.717
Hs Code.:

Synonyms:(4R,4aR,6S,7S,8aS)-2-(tert-butoxycarbonyl)-4-[3-(1,3-dioxolan-2-yl)propyl]-7-hydroxy-6,4-(iminomethano)-9-(p-toluenesulfonyl)perhydroisoquinoline

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Chemical Property of (4R,4aR,6S,7S,8aS)-2-(tert-butoxycarbonyl)-4-[3-(1,3-dioxolan-2-yl)propyl]-7-hydroxy-6,4-(iminomethano)-9-(p-toluenesulfonyl)perhydroisoquinoline

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Technology Process of (4R,4aR,6S,7S,8aS)-2-(tert-butoxycarbonyl)-4-[3-(1,3-dioxolan-2-yl)propyl]-7-hydroxy-6,4-(iminomethano)-9-(p-toluenesulfonyl)perhydroisoquinoline

There total 19 articles about (4R,4aR,6S,7S,8aS)-2-(tert-butoxycarbonyl)-4-[3-(1,3-dioxolan-2-yl)propyl]-7-hydroxy-6,4-(iminomethano)-9-(p-toluenesulfonyl)perhydroisoquinoline 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:

: C₂₁H₃₆N₂O₅

: 98-59-9
p-toluenesulfonyl chloride

: 1428872-52-9
(4R,4aR,6S,7S,8aS)-2-(tert-butoxycarbonyl)-4-[3-(1,3-dioxolan-2-yl)propyl]-7-hydroxy-6,4-(iminomethano)-9-(p-toluenesulfonyl)perhydroisoquinoline

Guidance literature:: C₂₁H₃₆N₂O₅; With triethylamine; In dichloromethane; at 0 ℃; Inert atmosphere;

p-toluenesulfonyl chloride; In dichloromethane; at 0 ℃; for 2.5h; Inert atmosphere;
DOI:10.1039/c3cc41104d

Reference yield:

: C₂₁H₃₄N₄O₅

: 1428872-52-9
(4R,4aR,6S,7S,8aS)-2-(tert-butoxycarbonyl)-4-[3-(1,3-dioxolan-2-yl)propyl]-7-hydroxy-6,4-(iminomethano)-9-(p-toluenesulfonyl)perhydroisoquinoline

Guidance literature:: Multi-step reaction with 2 steps

1.1: trimethylphosphane / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere

2.2: 2.5 h / 0 °C / Inert atmosphere

With triethylamine; trimethylphosphane; In tetrahydrofuran; dichloromethane;
DOI:10.1039/c3cc41104d

Reference yield:

: 1428872-47-2
(3R,6R,6aR,10aS,10bR)-6-[3-(1,3-dioxolan-2-yl)propyl]-6-(methoxycarbonyl)-5-oxo-3-phenyl-2,3,6,6a,7,10,10a,10b-octahydro-5H-oxazolo[3,2-a]isoquinoline

: 1428872-52-9
(4R,4aR,6S,7S,8aS)-2-(tert-butoxycarbonyl)-4-[3-(1,3-dioxolan-2-yl)propyl]-7-hydroxy-6,4-(iminomethano)-9-(p-toluenesulfonyl)perhydroisoquinoline

Guidance literature:: Multi-step reaction with 8 steps

1.1: ammonia; sodium / tetrahydrofuran / 0.03 h / -78 - -33 °C / Inert atmosphere; Cooling with acetone-dry ice

2.1: lithium aluminium tetrahydride / 1,4-dioxane / Inert atmosphere; Reflux

3.1: dichloromethane / 20 h / 20 °C / Inert atmosphere

4.1: triethylamine / 0 °C / Inert atmosphere

4.2: 4 h / 20 °C / Inert atmosphere

5.1: sodium azide / N,N-dimethyl-formamide / 72 h / 90 °C / Inert atmosphere

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

7.1: trimethylphosphane / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

8.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere

8.2: 2.5 h / 0 °C / Inert atmosphere

With lithium aluminium tetrahydride; sodium azide; ammonia; sodium; triethylamine; 3-chloro-benzenecarboperoxoic acid; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/c3cc41104d