N-benzyl-8β-<1-hydroxy-2-(trimethylsilyl)ethyl>-7α-<<(tert-butyldimethylsilyl)oxy>methyl>-endo-ethylenetetrahydronorthebaine

Base Information

Chemical Name:N-benzyl-8β-<1-hydroxy-2-(trimethylsilyl)ethyl>-7α-<<(tert-butyldimethylsilyl)oxy>methyl>-endo-ethylenetetrahydronorthebaine
CAS No.:110143-25-4
Molecular Formula:C₃₉H₅₇NO₅Si₂
Molecular Weight:676.056
Hs Code.:

Synonyms:N-benzyl-8β-<1-hydroxy-2-(trimethylsilyl)ethyl>-7α-<<(tert-butyldimethylsilyl)oxy>methyl>-endo-ethylenetetrahydronorthebaine

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Chemical Property of N-benzyl-8β-<1-hydroxy-2-(trimethylsilyl)ethyl>-7α-<<(tert-butyldimethylsilyl)oxy>methyl>-endo-ethylenetetrahydronorthebaine

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Technology Process of N-benzyl-8β-<1-hydroxy-2-(trimethylsilyl)ethyl>-7α-<<(tert-butyldimethylsilyl)oxy>methyl>-endo-ethylenetetrahydronorthebaine

There total 8 articles about N-benzyl-8β-<1-hydroxy-2-(trimethylsilyl)ethyl>-7α-<<(tert-butyldimethylsilyl)oxy>methyl>-endo-ethylenetetrahydronorthebaine 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: 84.0%

: 13170-43-9
(trimethylsilyl)methylmagnesium chloride

: 110143-26-5
N-benzyl-8β-formyl-7α-<<(tert-butyldimethylsilyl)oxy>methyl>-endo-ethylenetetrahydronorthebaine

: 110143-25-4
N-benzyl-8β-<1-hydroxy-2-(trimethylsilyl)ethyl>-7α-<<(tert-butyldimethylsilyl)oxy>methyl>-endo-ethylenetetrahydronorthebaine

Guidance literature:: In tetrahydrofuran; for 25h; Ambient temperature;
DOI:10.1021/jm00394a016

Reference yield:

: 93-97-0
benzoic acid anhydride

: 110143-25-4
N-benzyl-8β-<1-hydroxy-2-(trimethylsilyl)ethyl>-7α-<<(tert-butyldimethylsilyl)oxy>methyl>-endo-ethylenetetrahydronorthebaine

Guidance literature:: Multi-step reaction with 7 steps

1: 84 percent / Et₃N / CH₂Cl₂ / Ambient temperature

2: 99 percent / benzene / 7 h / Heating

3: 64 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / Heating

4: 1.) KH, 2.) n-BuLi

5: 97 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 - -40 °C

6: 52 percent / silica gel / CHCl₃ / 48 h

7: 84 percent / tetrahydrofuran / 25 h / Ambient temperature

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; silica gel; potassium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; chloroform; benzene;
DOI:10.1021/jm00394a016

Reference yield:

: 7679-18-7
N-desmethylthebaine hydrochloride

: 110143-25-4
N-benzyl-8β-<1-hydroxy-2-(trimethylsilyl)ethyl>-7α-<<(tert-butyldimethylsilyl)oxy>methyl>-endo-ethylenetetrahydronorthebaine

Guidance literature:: Multi-step reaction with 7 steps

1: 84 percent / Et₃N / CH₂Cl₂ / Ambient temperature

2: 99 percent / benzene / 7 h / Heating

3: 64 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / Heating

4: 1.) KH, 2.) n-BuLi

5: 97 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 - -40 °C

6: 52 percent / silica gel / CHCl₃ / 48 h

7: 84 percent / tetrahydrofuran / 25 h / Ambient temperature

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; silica gel; potassium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; chloroform; benzene;
DOI:10.1021/jm00394a016