[(S)-1-({(R)-Carbamoyl-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-methyl}-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(S)-1-({(R)-Carbamoyl-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-methyl}-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester
• CAS No.: 100682-99-3
• Molecular Formula: C₂₈H₃₁N₅O₉
• Molecular Weight: 581.582

Synonyms:[(S)-1-({(R)-Carbamoyl-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-methyl}-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester

Chemical Property of [(S)-1-({(R)-Carbamoyl-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-methyl}-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester

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Technology Process of [(S)-1-({(R)-Carbamoyl-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-methyl}-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester

There total 8 articles about [(S)-1-({(R)-Carbamoyl-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-methyl}-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl 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: 77.0%

1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-2',3'-O-cyclohexylidene-β-D-allo-furanosyluronic acid amide>uracil (100682-85-7) → [(S)-1-({(R)-Carbamoyl-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-methyl}-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester (100682-99-3)

Guidance literature:

With AG₅₀WX₈(H+); In 1,4-dioxane; water; for 16h; Heating;

DOI:10.1021/jo00362a027

Reference yield:

N-Cbz-L-Phe (1161-13-3) → [(S)-1-({(R)-Carbamoyl-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-methyl}-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester (100682-99-3)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol / 18 h / 25 °C

2: acetic acid / H₂O / 5 h

3: 77 percent / AG₅₀WX₈(H+) / dioxane; H₂O / 16 h / Heating

With AG₅₀WX₈(H+); acetic acid; In 1,4-dioxane; methanol; water;

DOI:10.1021/jo00362a027

Reference yield:

2',3'-O-cyclohexylideneuridine 5'-aldehyde (34311-30-3) → [(S)-1-({(R)-Carbamoyl-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-methyl}-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester (100682-99-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / 3A sieves / tetrahydrofuran / 2 h / Ambient temperature

2: methanol / 18 h / 25 °C

3: acetic acid / H₂O / 5 h

4: 77 percent / AG₅₀WX₈(H+) / dioxane; H₂O / 16 h / Heating

With 3 A molecular sieve; AG₅₀WX₈(H+); acetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; water;

DOI:10.1021/jo00362a027

upstream raw materials:

1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-2',3'-O-cyclohexylidene-β-D-allo-furanosyluronic acid amide>uracil

N-Cbz-L-Phe

2',3'-O-cyclohexylideneuridine-5'-methylimine

bezyloxycarbonyl-L-phenylalanyl anhydride

Downstream raw materials:

1-<5'-(L-phenylalanylmethylamino)-5'-deoxy-α-L-talo-furanosyluronic acid amide>uracil

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