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

Base Information

Chemical Name:tert-Butoxycarbonylamino-acetic acid 3-[(2R,4S,5R)-4-(4-chloro-benzyloxy)-5-(2-dimethylamino-acetoxymethyl)-tetrahydro-furan-2-yl]-5-fluoro-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester
CAS No.:150083-10-6
Molecular Formula:C₂₈H₃₆ClFN₄O₁₀
Molecular Weight:643.066
Hs Code.:

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

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

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

There total 5 articles about tert-Butoxycarbonylamino-acetic acid 3-[(2R,4S,5R)-4-(4-chloro-benzyloxy)-5-(2-dimethylamino-acetoxymethyl)-tetrahydro-furan-2-yl]-5-fluoro-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

: 150083-10-6
tert-Butoxycarbonylamino-acetic acid 3-[(2R,4S,5R)-4-(4-chloro-benzyloxy)-5-(2-dimethylamino-acetoxymethyl)-tetrahydro-furan-2-yl]-5-fluoro-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 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

5: 1.) 1-hydroxybenzotriazole, dicyclohexylcarbodiimide, 2.) N,N-dimethylaminopyridine / 1.) CH₃CN, RT, 3 h, 2.) CH₃CN, RT, 18 h

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

Reference yield:

: 34573-36-9
N-[(1,1-dimethylethoxy)carbonyl]glycine chloromethyl ester

: 150083-10-6
tert-Butoxycarbonylamino-acetic acid 3-[(2R,4S,5R)-4-(4-chloro-benzyloxy)-5-(2-dimethylamino-acetoxymethyl)-tetrahydro-furan-2-yl]-5-fluoro-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

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

2: 1.) 1-hydroxybenzotriazole, dicyclohexylcarbodiimide, 2.) N,N-dimethylaminopyridine / 1.) CH₃CN, RT, 3 h, 2.) CH₃CN, RT, 18 h

With dmap; potassium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; sodium iodide;
DOI:10.1248/cpb.44.1196

Reference yield:

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

: 150083-10-6
tert-Butoxycarbonylamino-acetic acid 3-[(2R,4S,5R)-4-(4-chloro-benzyloxy)-5-(2-dimethylamino-acetoxymethyl)-tetrahydro-furan-2-yl]-5-fluoro-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 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

4: 1.) 1-hydroxybenzotriazole, dicyclohexylcarbodiimide, 2.) N,N-dimethylaminopyridine / 1.) CH₃CN, RT, 3 h, 2.) CH₃CN, RT, 18 h

With dmap; potassium hydroxide; potassium carbonate; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; sodium iodide;
DOI:10.1248/cpb.44.1196