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

Base Information

• Chemical Name: 1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-α-L-talo-furanosyluronic acid>uracil
• CAS No.: 100682-91-5
• Molecular Formula: C₃₄H₃₈N₄O₁₀
• Molecular Weight: 662.697

Synonyms:1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-α-L-talo-furanosyluronic acid>uracil

Chemical Property of 1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-α-L-talo-furanosyluronic acid>uracil

Chemical Property:

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Technology Process of 1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-α-L-talo-furanosyluronic acid>uracil

There total 8 articles about 1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-α-L-talo-furanosyluronic 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: 39.0%

1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-2',3'-O-cyclohexylidene-β-D-allo-furanosyluronic acid amide>uracil (100682-85-7) → 1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-α-L-talo-furanosyluronic acid>uracil (100682-91-5)

Guidance literature:

With nitrosulfuric acid; In dichloromethane; for 0.5h;

DOI:10.1021/jo00362a027

Reference yield:

N-Cbz-L-Phe (1161-13-3) → 1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-α-L-talo-furanosyluronic acid>uracil (100682-91-5)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol / 18 h / 25 °C

2: acetic acid / H₂O / 5 h

3: 39 percent / nitrosulfuric acid / CH₂Cl₂ / 0.5 h

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

DOI:10.1021/jo00362a027

Reference yield:

2',3'-O-cyclohexylideneuridine 5'-aldehyde (34311-30-3) → 1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-α-L-talo-furanosyluronic acid>uracil (100682-91-5)

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: 39 percent / nitrosulfuric acid / CH₂Cl₂ / 0.5 h

With 3 A molecular sieve; nitrosulfuric acid; acetic acid; In tetrahydrofuran; methanol; dichloromethane; 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:

(R)-[((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

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

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