N-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methyltetrahydrofuran-3-yl)-2,2,2-trifluoroacetamide

Base Information

Chemical Name:N-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methyltetrahydrofuran-3-yl)-2,2,2-trifluoroacetamide
CAS No.:1439900-76-1
Molecular Formula:C₂₆H₂₆F₃N₃O₆
Molecular Weight:533.504
Hs Code.:

Synonyms:N-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methyltetrahydrofuran-3-yl)-2,2,2-trifluoroacetamide

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Chemical Property of N-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methyltetrahydrofuran-3-yl)-2,2,2-trifluoroacetamide

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Technology Process of N-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methyltetrahydrofuran-3-yl)-2,2,2-trifluoroacetamide

There total 10 articles about N-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methyltetrahydrofuran-3-yl)-2,2,2-trifluoroacetamide 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: 21.0%

: 1439900-73-8
N-((2S,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxy-3-methyltetrahydrofuran-3-yl)-2,2,2-trifluoroacetamide

: 66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6
uracil

: 1439900-76-1
N-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methyltetrahydrofuran-3-yl)-2,2,2-trifluoroacetamide

Guidance literature:: uracil; With N,O-bis(trimethylsilyl)acetamide; In acetonitrile; at 85 ℃; for 0.5h;

N-((2S,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxy-3-methyltetrahydrofuran-3-yl)-2,2,2-trifluoroacetamide; In acetonitrile; at 0 - 20 ℃;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 80 ℃; for 21h;

Reference yield:

: N-((2S,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxy-3-methyltetrahydrofuran-3-yl)-2-methylpropane-2-sulfinamide

: 1439900-76-1
N-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methyltetrahydrofuran-3-yl)-2,2,2-trifluoroacetamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: hydrogenchloride / 1,4-dioxane / 1 h / 0 - 20 °C

1.2: 3 h / -40 - 20 °C

2.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.5 h / 85 °C

2.2: 0 - 20 °C

2.3: 21 h / 80 °C

With hydrogenchloride; N,O-bis(trimethylsilyl)acetamide; In 1,4-dioxane; acetonitrile;

Reference yield:

: 52485-92-4
methyl α-D-ribofuranoside

: 1439900-76-1
N-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methyltetrahydrofuran-3-yl)-2,2,2-trifluoroacetamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 0 °C

1.2: 16 h / 0 - 20 °C

2.1: tin(IV) chloride / dichloromethane / 24 h / 0 °C

3.1: Dess-Martin periodane / dichloromethane / 24 h / 0 - 20 °C

4.1: titanium(IV) tetraethanolate / tetrahydrofuran / 6 h / 20 - 60 °C

5.1: tetrahydrofuran / 0.5 h / -78 °C

6.1: hydrogenchloride / 1,4-dioxane / 1 h / 0 - 20 °C

7.1: pyridine / dichloromethane / 3 h / -40 - 20 °C

8.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 85 °C

8.2: 21 h / 0 - 80 °C

With pyridine; hydrogenchloride; titanium(IV) tetraethanolate; N,O-bis-(trimethylsilyl)-acetamide; tin(IV) chloride; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;