(S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid 5-fluoro-3-[(2R,4S,5R)-4-(4-fluoro-benzyloxy)-5-hydroxymethyl-tetrahydro-furan-2-yl]-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester

Base Information

Chemical Name:(S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid 5-fluoro-3-[(2R,4S,5R)-4-(4-fluoro-benzyloxy)-5-hydroxymethyl-tetrahydro-furan-2-yl]-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester
CAS No.:179744-33-3
Molecular Formula:C₂₇H₃₅F₂N₃O₉
Molecular Weight:583.586
Hs Code.:

(S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid 5-fluoro-3-[(2R,4S,5R)-4-(4-fluoro-benzyloxy)-5-hydroxymethyl-tetrahydro-furan-2-yl]-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester

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Chemical Property of (S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid 5-fluoro-3-[(2R,4S,5R)-4-(4-fluoro-benzyloxy)-5-hydroxymethyl-tetrahydro-furan-2-yl]-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester

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Technology Process of (S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid 5-fluoro-3-[(2R,4S,5R)-4-(4-fluoro-benzyloxy)-5-hydroxymethyl-tetrahydro-furan-2-yl]-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester

There total 5 articles about (S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid 5-fluoro-3-[(2R,4S,5R)-4-(4-fluoro-benzyloxy)-5-hydroxymethyl-tetrahydro-furan-2-yl]-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl 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:

: 50-91-9
5-Fluoro-2'-deoxyuridine

: 179744-33-3
(S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid 5-fluoro-3-[(2R,4S,5R)-4-(4-fluoro-benzyloxy)-5-hydroxymethyl-tetrahydro-furan-2-yl]-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 77 percent / imidazole / dimethylformamide / 5.5 h / -30 °C

2: 1.) aq. KOH / 1.) toluene, dioxane, RT, 2.5 h, 2.) toluene, dioxane, RT, 6 h

3: aq. AcOH / 5 h / 40 °C

4: 1.) NaI, 2.) K₂CO₃ / 1.) acetone, RT, 1 h, 2.) acetone, RT, 20 h

With 1H-imidazole; potassium hydroxide; potassium carbonate; acetic acid; sodium iodide; In N,N-dimethyl-formamide;
DOI:10.1248/cpb.44.1196

Reference yield:

: 129816-30-4
5'-O-(tert-butyldimethylsilyl)-2'-deoxy-5-fluorouridine

: 179744-33-3
(S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid 5-fluoro-3-[(2R,4S,5R)-4-(4-fluoro-benzyloxy)-5-hydroxymethyl-tetrahydro-furan-2-yl]-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) aq. KOH / 1.) toluene, dioxane, RT, 2.5 h, 2.) toluene, dioxane, RT, 6 h

2: aq. AcOH / 5 h / 40 °C

3: 1.) NaI, 2.) K₂CO₃ / 1.) acetone, RT, 1 h, 2.) acetone, RT, 20 h

With potassium hydroxide; potassium carbonate; acetic acid; sodium iodide;
DOI:10.1248/cpb.44.1196

Reference yield:

: 459-46-1
4-Fluorobenzyl bromide

: 179744-33-3
(S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid 5-fluoro-3-[(2R,4S,5R)-4-(4-fluoro-benzyloxy)-5-hydroxymethyl-tetrahydro-furan-2-yl]-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) aq. KOH / 1.) toluene, dioxane, RT, 2.5 h, 2.) toluene, dioxane, RT, 6 h

2: aq. AcOH / 5 h / 40 °C

3: 1.) NaI, 2.) K₂CO₃ / 1.) acetone, RT, 1 h, 2.) acetone, RT, 20 h

With potassium hydroxide; potassium carbonate; acetic acid; sodium iodide;
DOI:10.1248/cpb.44.1196