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

Base Information

• Chemical Name: (1S,5R,6R,8S)-2-benzyl-6-(4-bromophenyl)-8-[(tert-butyldimethylsilyloxy)methyl]-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one
• CAS No.: 1631977-83-7
• Molecular Formula: C₂₆H₃₄BrNO₄Si
• Molecular Weight: 532.55

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

Chemical Property of (1S,5R,6R,8S)-2-benzyl-6-(4-bromophenyl)-8-[(tert-butyldimethylsilyloxy)methyl]-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one

Chemical Property:

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Technology Process of (1S,5R,6R,8S)-2-benzyl-6-(4-bromophenyl)-8-[(tert-butyldimethylsilyloxy)methyl]-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one

There total 2 articles about (1S,5R,6R,8S)-2-benzyl-6-(4-bromophenyl)-8-[(tert-butyldimethylsilyloxy)methyl]-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one 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: 82.0%

C20H20BrNO4 (1631977-87-1) + tert-butyldimethylsilyl chloride (18162-48-6) → (1S,5R,6R,8S)-2-benzyl-6-(4-bromophenyl)-8-[(tert-butyldimethylsilyloxy)methyl]-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one (1631977-83-7)

Guidance literature:

With 1H-imidazole; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere;

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 → (1S,5R,6R,8S)-2-benzyl-6-(4-bromophenyl)-8-[(tert-butyldimethylsilyloxy)methyl]-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one (1631977-83-7)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 1H-imidazole; tin(IV) chloride; In tetrahydrofuran; acetonitrile;

DOI:10.3762/bjoc.10.182

Reference yield: 73.0%

(1S,5R,6R,8S)-2-benzyl-6-(4-bromophenyl)-8-[(tert-butyldimethylsilyloxy)methyl]-3,7-dioxa-2-azabicyclo[3.3.1]nonan-9-one (1631977-83-7) → (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 (1631977-84-8)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -10 ℃; for 1h; Inert atmosphere;

DOI:10.3762/bjoc.10.182

upstream raw materials:

C₂₀H₂₀BrNO₄

tert-butyldimethylsilyl chloride

Downstream raw materials:

(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

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

(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

C₅₈H₇₆N₂O₈Si₂

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