1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-5'-cyano-2',3'-cyclohexylidene-α-L-talo-furanosyl>uracil

Base Information

• Chemical Name: 1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-5'-cyano-2',3'-cyclohexylidene-α-L-talo-furanosyl>uracil
• CAS No.: 100682-90-4
• Molecular Formula: C₃₄H₃₇N₅O₈
• Molecular Weight: 643.696

Synonyms:1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-5'-cyano-2',3'-cyclohexylidene-α-L-talo-furanosyl>uracil

Chemical Property of 1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-5'-cyano-2',3'-cyclohexylidene-α-L-talo-furanosyl>uracil

Chemical Property:

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Technology Process of 1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-5'-cyano-2',3'-cyclohexylidene-α-L-talo-furanosyl>uracil

There total 3 articles about 1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-5'-cyano-2',3'-cyclohexylidene-α-L-talo-furanosyl>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:

N-Cbz-L-Phe (1161-13-3) → 1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-5'-cyano-2',3'-cyclohexylidene-α-L-talo-furanosyl>uracil (100682-90-4)

Guidance literature:

Multi-step reaction with 2 steps

1: N-methylmorpholine / CH₂Cl₂ / 2 h / -20 °C

2: CH₂Cl₂ / 16 h / -20 °C

With 4-methyl-morpholine; In dichloromethane;

DOI:10.1021/jo00362a027

Reference yield:

bezyloxycarbonyl-L-phenylalanyl anhydride (913971-35-4) + C17H22N4O5 (100682-88-0) → 1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-5'-cyano-2',3'-cyclohexylidene-α-L-talo-furanosyl>uracil (100682-90-4)

Guidance literature:

In dichloromethane; at -20 ℃; for 16h; Yield given;

DOI:10.1021/jo00362a027

Reference yield:

2',3'-O-cyclohexylideneuridine 5'-aldehyde (34311-30-3) → 1-<5'-(L-carbobenzyloxyphenylalanylmethylamino)-5'-deoxy-5'-cyano-2',3'-cyclohexylidene-α-L-talo-furanosyl>uracil (100682-90-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 37 percent / methanol; H₂O / 16 h

2: CH₂Cl₂ / 16 h / -20 °C

In methanol; dichloromethane; water;

DOI:10.1021/jo00362a027

upstream raw materials:

bezyloxycarbonyl-L-phenylalanyl anhydride

C₁₇H₂₂N₄O₅

N-Cbz-L-Phe

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

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

[(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

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

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

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