1-((3S,4aR,6R,7R,8aR)-6,7-bis(benzyloxy)-3-((tert-butyldimethylsilyloxy)methyl)octahydroisoquinolin-2-(1H)-yl)-2,2,2-trifluoroethanone

Base Information

Chemical Name:1-((3S,4aR,6R,7R,8aR)-6,7-bis(benzyloxy)-3-((tert-butyldimethylsilyloxy)methyl)octahydroisoquinolin-2-(1H)-yl)-2,2,2-trifluoroethanone
CAS No.:1312224-56-8
Molecular Formula:C₃₂H₄₄F₃NO₄Si
Molecular Weight:591.786
Hs Code.:

Synonyms:1-((3S,4aR,6R,7R,8aR)-6,7-bis(benzyloxy)-3-((tert-butyldimethylsilyloxy)methyl)octahydroisoquinolin-2-(1H)-yl)-2,2,2-trifluoroethanone

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Chemical Property of 1-((3S,4aR,6R,7R,8aR)-6,7-bis(benzyloxy)-3-((tert-butyldimethylsilyloxy)methyl)octahydroisoquinolin-2-(1H)-yl)-2,2,2-trifluoroethanone

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MSDS Files:: SDS file from LookChem

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Technology Process of 1-((3S,4aR,6R,7R,8aR)-6,7-bis(benzyloxy)-3-((tert-butyldimethylsilyloxy)methyl)octahydroisoquinolin-2-(1H)-yl)-2,2,2-trifluoroethanone

There total 14 articles about 1-((3S,4aR,6R,7R,8aR)-6,7-bis(benzyloxy)-3-((tert-butyldimethylsilyloxy)methyl)octahydroisoquinolin-2-(1H)-yl)-2,2,2-trifluoroethanone 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: 95.0%

: 1312224-65-9
N-((S)-1-((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(hydroxymethyl)cyclohexyl)-3-(tert-butyldimethylsilyloxy)propan-2-yl)-2,2,2-trifluoroacetamide

: 1312224-56-8
1-((3S,4aR,6R,7R,8aR)-6,7-bis(benzyloxy)-3-((tert-butyldimethylsilyloxy)methyl)octahydroisoquinolin-2-(1H)-yl)-2,2,2-trifluoroethanone

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1039/c1ob05219e

Reference yield:

: 956006-11-4
(S)-3-((S)-1-((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(hydroxymethyl)cyclohexyl)-3-(tert-butyldimethylsilyloxy)propan-2-ylamino)-4-benzyloxazolidin-2-one

: 1312224-56-8
1-((3S,4aR,6R,7R,8aR)-6,7-bis(benzyloxy)-3-((tert-butyldimethylsilyloxy)methyl)octahydroisoquinolin-2-(1H)-yl)-2,2,2-trifluoroethanone

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: samarium diiodide / tetrahydrofuran; methanol / Inert atmosphere

3.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With n-butyllithium; samarium diiodide; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; methanol; hexane; 3.1: Mitsunobu reaction;
DOI:10.1039/c1ob05219e

Reference yield:

: 956006-07-8
((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(iodomethyl)cyclohexyl)methanol

: 1312224-56-8
1-((3S,4aR,6R,7R,8aR)-6,7-bis(benzyloxy)-3-((tert-butyldimethylsilyloxy)methyl)octahydroisoquinolin-2-(1H)-yl)-2,2,2-trifluoroethanone

Guidance literature:: Multi-step reaction with 4 steps

1.1: indium(III) chloride / dichloromethane / 0.67 h / 20 °C / Inert atmosphere

1.2: Inert atmosphere; UV-irradiation

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: samarium diiodide / tetrahydrofuran; methanol / Inert atmosphere

4.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With indium(III) chloride; n-butyllithium; samarium diiodide; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; 4.1: Mitsunobu reaction;
DOI:10.1039/c1ob05219e