4-amino-1-[5-[4-(4-bromo-phenyl)-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yloxymethyl]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1H-pyrimidin-2-one

Base Information

• Chemical Name: 4-amino-1-[5-[4-(4-bromo-phenyl)-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yloxymethyl]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1H-pyrimidin-2-one
• CAS No.: 928780-21-6
• Molecular Formula: C₃₀H₄₉BrN₃O₈PSi₂
• Molecular Weight: 746.783

Synonyms:4-amino-1-[5-[4-(4-bromo-phenyl)-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yloxymethyl]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1H-pyrimidin-2-one

Chemical Property of 4-amino-1-[5-[4-(4-bromo-phenyl)-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yloxymethyl]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1H-pyrimidin-2-one

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Technology Process of 4-amino-1-[5-[4-(4-bromo-phenyl)-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yloxymethyl]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1H-pyrimidin-2-one

There total 4 articles about 4-amino-1-[5-[4-(4-bromo-phenyl)-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yloxymethyl]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1H-pyrimidin-2-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: 51.0%

trans-4-(4-bromophenyl)-2-(4-nitrophenoxy)-2-oxido-1,3,2-dioxaphosphorinane + 1-[2',3'-di-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine (87418-91-5) → 4-amino-1-[5-[4-(4-bromo-phenyl)-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yloxymethyl]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1H-pyrimidin-2-one (928780-21-6)

Guidance literature:

1-[2',3'-di-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine; With tert-butylmagnesium chloride; In tetrahydrofuran; at 20 ℃; for 0.5h;

trans-4-(4-bromophenyl)-2-(4-nitrophenoxy)-2-oxido-1,3,2-dioxaphosphorinane; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1021/jm0607449

Reference yield:

(-)-ethyl 3-(4-bromophenyl)-3-hydroxypropionate (70200-16-7) → 4-amino-1-[5-[4-(4-bromo-phenyl)-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yloxymethyl]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1H-pyrimidin-2-one (928780-21-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 3.3 g / LiAlH₄ / diethyl ether / 0 - 20 °C

2.1: Et₃N / tetrahydrofuran / 2 h / Heating

2.2: 60 percent / sodium 4-nitrophenoxide / tetrahydrofuran / 1.5 h / Heating

3.1: t-BuMgCl / tetrahydrofuran / 0.5 h / 20 °C

3.2: 51 percent / tetrahydrofuran / 18 h / 20 °C

With lithium aluminium tetrahydride; tert-butylmagnesium chloride; triethylamine; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jm0607449

Reference yield:

4-bromo-benzaldehyde (1122-91-4) → 4-amino-1-[5-[4-(4-bromo-phenyl)-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yloxymethyl]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1H-pyrimidin-2-one (928780-21-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C

2.1: 3.3 g / LiAlH₄ / diethyl ether / 0 - 20 °C

3.1: Et₃N / tetrahydrofuran / 2 h / Heating

3.2: 60 percent / sodium 4-nitrophenoxide / tetrahydrofuran / 1.5 h / Heating

4.1: t-BuMgCl / tetrahydrofuran / 0.5 h / 20 °C

4.2: 51 percent / tetrahydrofuran / 18 h / 20 °C

With lithium aluminium tetrahydride; tert-butylmagnesium chloride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1021/jm0607449

upstream raw materials:

1-[2',3'-di-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine

(-)-ethyl 3-(4-bromophenyl)-3-hydroxypropionate

4-bromo-benzaldehyde

1-(4-bromophenyl)-1,3-propanediol

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