4-{2-[5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethoxy]-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-4-yl}-benzoic acid methyl ester

Base Information

• Chemical Name: 4-{2-[5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethoxy]-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-4-yl}-benzoic acid methyl ester
• CAS No.: 928780-48-7
• Molecular Formula: C₃₂H₅₂N₃O₁₀PSi₂
• Molecular Weight: 725.924

Synonyms:4-{2-[5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethoxy]-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-4-yl}-benzoic acid methyl ester

Chemical Property of 4-{2-[5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethoxy]-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-4-yl}-benzoic acid methyl ester

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Technology Process of 4-{2-[5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethoxy]-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-4-yl}-benzoic acid methyl ester

There total 5 articles about 4-{2-[5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethoxy]-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-4-yl}-benzoic acid methyl ester 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: 62.0%

trans-4-(4-methoxycarbonylphenyl)-2-(4-nitrophenoxy)-2-oxido-1,3,2-dioxaphosphorinane + 1-[2',3'-di-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine (87418-91-5) → 4-{2-[5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethoxy]-2-oxo-2λ5-[1,3,2]dioxaphosphinan-4-yl}-benzoic acid methyl ester (928780-48-7)

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

DOI:10.1021/jm0607449

Reference yield:

4-(1,3-dihydroxypropyl)benzoic acid methyl ester (862187-65-3) → 4-{2-[5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethoxy]-2-oxo-2λ5-[1,3,2]dioxaphosphinan-4-yl}-benzoic acid methyl ester (928780-48-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₃N / tetrahydrofuran / 2 h / Heating

1.2: 23 percent / sodium 4-nitrophenoxide / tetrahydrofuran / 1.5 h / Heating

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

2.2: 62 percent / tetrahydrofuran / 18 h / 20 °C

With tert-butylmagnesium chloride; triethylamine; In tetrahydrofuran;

DOI:10.1021/jm0607449

Reference yield:

(-)-ethyl 3-(4-bromophenyl)-3-hydroxypropionate (70200-16-7) → 4-{2-[5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethoxy]-2-oxo-2λ5-[1,3,2]dioxaphosphinan-4-yl}-benzoic acid methyl ester (928780-48-7)

Guidance literature:

Multi-step reaction with 4 steps

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

2.1: 87 percent / Et₃N; Pd(PPh₃)2Cl₂ / 24 h / 85 °C / 2844.31 Torr

3.1: Et₃N / tetrahydrofuran / 2 h / Heating

3.2: 23 percent / sodium 4-nitrophenoxide / tetrahydrofuran / 1.5 h / Heating

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

4.2: 62 percent / tetrahydrofuran / 18 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; lithium aluminium tetrahydride; tert-butylmagnesium chloride; triethylamine; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jm0607449

upstream raw materials:

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

4-(1,3-dihydroxypropyl)benzoic acid methyl ester

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

4-bromo-benzaldehyde

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