1-<5'-(L-phenylalanylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil

Base Information

• Chemical Name: 1-<5'-(L-phenylalanylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil
• CAS No.: 100682-76-6
• Molecular Formula: C₂₀H₂₄N₄O₈
• Molecular Weight: 448.433

Synonyms:1-<5'-(L-phenylalanylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil

Chemical Property of 1-<5'-(L-phenylalanylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil

Chemical Property:

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Technology Process of 1-<5'-(L-phenylalanylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil

There total 7 articles about 1-<5'-(L-phenylalanylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil 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: 54.0%

(S)-[((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-methyl-amino]-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic acid (100682-98-2) → 1-<5'-(L-phenylalanylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil (100682-76-6)

Guidance literature:

With formic acid; palladium; In methanol; for 0.5h; Ambient temperature;

DOI:10.1021/jo00362a027

Reference yield:

N-Cbz-L-Phe (1161-13-3) → 1-<5'-(L-phenylalanylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil (100682-76-6)

Guidance literature:

Multi-step reaction with 5 steps

1: methanol / 18 h / 25 °C

2: acetic acid / H₂O / 5 h

3: 51 percent / nitrosulfuric acid / CH₂Cl₂; H₂O / 0.5 h

4: 70 percent / 50 percent aq. HOAc / 3 h / Heating

5: 54 percent / HCO₂H / Pd black / methanol / 0.5 h / Ambient temperature

With formic acid; nitrosulfuric acid; acetic acid; palladium; In methanol; dichloromethane; water;

DOI:10.1021/jo00362a027

Reference yield:

2',3'-O-cyclohexylideneuridine-5'-methylimine (100682-84-6) → 1-<5'-(L-phenylalanylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil (100682-76-6)

Guidance literature:

Multi-step reaction with 5 steps

1: methanol / 18 h / 25 °C

2: acetic acid / H₂O / 5 h

3: 51 percent / nitrosulfuric acid / CH₂Cl₂; H₂O / 0.5 h

4: 70 percent / 50 percent aq. HOAc / 3 h / Heating

5: 54 percent / HCO₂H / Pd black / methanol / 0.5 h / Ambient temperature

With formic acid; nitrosulfuric acid; acetic acid; palladium; In methanol; dichloromethane; water;

DOI:10.1021/jo00362a027

upstream raw materials:

(S)-[((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-methyl-amino]-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic acid

N-Cbz-L-Phe

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

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

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