N-(1-((2S,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

Base Information

Chemical Name:N-(1-((2S,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide
CAS No.:1583260-53-0
Molecular Formula:C₃₀H₃₈FN₃O₅Si
Molecular Weight:567.733
Hs Code.:

N-(1-((2S,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

Synonyms:N-(1-((2S,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

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Chemical Property of N-(1-((2S,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

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Technology Process of N-(1-((2S,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

There total 8 articles about N-(1-((2S,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide 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%

: (3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyldihydrofuran-2-yl acetate

: 238096-55-4
N-(2-((1-trimethylsilyl)oxy)pyrimidin-4-yl)benzamide

: 1583260-54-1
N-(1-((2R,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

: 1583260-53-0
N-(1-((2S,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

Guidance literature:: With tin(IV) chloride; In chlorobenzene; at 70 ℃; for 15h; diastereoselective reaction;
DOI:10.1021/ja502205q

Reference yield:

: 1583260-50-7
(3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyldihydrofuran-2(3H)-one

: 1583260-54-1
N-(1-((2R,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

: 1583260-53-0
N-(1-((2S,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

Guidance literature:: Multi-step reaction with 3 steps

1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -78 °C

2: dmap; pyridine / dichloromethane / -78 - 0 °C

3: tin(IV) chloride / chlorobenzene / 15 h / 70 °C

With pyridine; dmap; tin(IV) chloride; diisobutylaluminium hydride; In dichloromethane; chlorobenzene; toluene;
DOI:10.1021/ja502205q

Reference yield:

: C₁₉H₃₁FO₄Si

: 1583260-54-1
N-(1-((2R,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

: 1583260-53-0
N-(1-((2S,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

Guidance literature:: Multi-step reaction with 2 steps

1: dmap; pyridine / dichloromethane / -78 - 0 °C

2: tin(IV) chloride / chlorobenzene / 15 h / 70 °C

With pyridine; dmap; tin(IV) chloride; In dichloromethane; chlorobenzene;
DOI:10.1021/ja502205q