(1S,2R,4S,5R,8S)-6-benzyl-2-(4-bromophenyl)-4-[(tert-butyldimethylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.2.1]octan-8-ol

Base Information

Chemical Name:(1S,2R,4S,5R,8S)-6-benzyl-2-(4-bromophenyl)-4-[(tert-butyldimethylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.2.1]octan-8-ol
CAS No.:1631977-97-3
Molecular Formula:C₂₆H₃₆BrNO₃Si
Molecular Weight:518.566
Hs Code.:

Synonyms:(1S,2R,4S,5R,8S)-6-benzyl-2-(4-bromophenyl)-4-[(tert-butyldimethylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.2.1]octan-8-ol

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Chemical Property of (1S,2R,4S,5R,8S)-6-benzyl-2-(4-bromophenyl)-4-[(tert-butyldimethylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.2.1]octan-8-ol

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Technology Process of (1S,2R,4S,5R,8S)-6-benzyl-2-(4-bromophenyl)-4-[(tert-butyldimethylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.2.1]octan-8-ol

There total 4 articles about (1S,2R,4S,5R,8S)-6-benzyl-2-(4-bromophenyl)-4-[(tert-butyldimethylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.2.1]octan-8-ol 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: 79.0%

: 1631977-84-8
(1R,5S,6R,8S,9R)-2-benzyl-6-(4-bromophenyl)-8-[(tert-butyldimethylsilyloxy)methyl]-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-ol

: 1631977-97-3
(1S,2R,4S,5R,8S)-6-benzyl-2-(4-bromophenyl)-4-[(tert-butyldimethylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.2.1]octan-8-ol

: (2S,3R,4R,5S,6R)-3-(benzylamino)-6-(4-bromophenyl)-2-[(tert-butyldimethylsilyloxy)methyl]-5-(hydroxymethyl)tetrahydro-2H-pyran-4-ol

Guidance literature:: With samarium diiodide; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;
DOI:10.3762/bjoc.10.182

Reference yield:

: 1631977-87-1
C₂₀H₂₀BrNO₄

: 1631977-97-3
(1S,2R,4S,5R,8S)-6-benzyl-2-(4-bromophenyl)-4-[(tert-butyldimethylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.2.1]octan-8-ol

: (2S,3R,4R,5S,6R)-3-(benzylamino)-6-(4-bromophenyl)-2-[(tert-butyldimethylsilyloxy)methyl]-5-(hydroxymethyl)tetrahydro-2H-pyran-4-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 1H-imidazole / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

2: L-Selectride / tetrahydrofuran / 1 h / -10 °C / Inert atmosphere

3: samarium diiodide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

With 1H-imidazole; samarium diiodide; L-Selectride; In tetrahydrofuran;
DOI:10.3762/bjoc.10.182

Reference yield:

: (3S)-2-benzyl-3-[(4S)-2-(4-bromophenyl)-1,3-dioxolan-4-yl]-4-[2-(trimethylsilyl)-ethoxy]-3,6-dihydro-2H-1,2-oxazine

: 1631977-97-3
(1S,2R,4S,5R,8S)-6-benzyl-2-(4-bromophenyl)-4-[(tert-butyldimethylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.2.1]octan-8-ol

: (2S,3R,4R,5S,6R)-3-(benzylamino)-6-(4-bromophenyl)-2-[(tert-butyldimethylsilyloxy)methyl]-5-(hydroxymethyl)tetrahydro-2H-pyran-4-ol

Guidance literature:: Multi-step reaction with 4 steps

1: tin(IV) chloride / acetonitrile / 18 h / -30 °C / Inert atmosphere

2: 1H-imidazole / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

3: L-Selectride / tetrahydrofuran / 1 h / -10 °C / Inert atmosphere

4: samarium diiodide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

With 1H-imidazole; samarium diiodide; tin(IV) chloride; L-Selectride; In tetrahydrofuran; acetonitrile;
DOI:10.3762/bjoc.10.182