1-[(1R,3S,5S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-yl]uracil

Base Information

• Chemical Name: 1-[(1R,3S,5S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-yl]uracil
• CAS No.: 881423-93-4
• Molecular Formula: C₁₇H₁₈N₂O₆
• Molecular Weight: 346.34

Synonyms:1-[(1R,3S,5S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-yl]uracil

Chemical Property of 1-[(1R,3S,5S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-yl]uracil

Chemical Property:

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Technology Process of 1-[(1R,3S,5S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-yl]uracil

There total 1 articles about 1-[(1R,3S,5S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-yl]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: 96.0%

(1'S,3'R,4'R,5'R,7'S)-N4-benzoyl-1-(4'-hydroxy-3'-hydroxymethyl-1'-phenyl-2',6'-dioxabicyclo[3.3.0]oct-7'-yl)cytosine (660410-96-8) → 1-[(1R,3S,5S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-yl]uracil (881423-93-4)

Guidance literature:

With water; sodium hydrogensulfite; sodium sulfite; In 1,4-dioxane; at 80 ℃; for 24h;

DOI:10.1021/jo052413u

Reference yield:

1-[(1R,3S,5S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-yl]uracil (881423-93-4) → Diisopropyl-phosphoramidous acid (2R,3R,3aR,5S,6aS)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6a-phenyl-hexahydro-furo[3,2-b]furan-3-yl ester 2-cyano-ethyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 1 h

2: i-Pr₂NEt / CH₂Cl₂ / 1 h / 0 °C

With pyridine; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jo052413u

Reference yield:

1-[(1R,3S,5S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-yl]uracil (881423-93-4) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 1-{(2S,3aS,5R,6R,6aR)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-6-hydroxy-3a-phenyl-hexahydro-furo[3,2-b]furan-2-yl}-1H-pyrimidine-2,4-dione

Guidance literature:

With pyridine; for 1h;

DOI:10.1021/jo052413u

upstream raw materials:

(1'S,3'R,4'R,5'R,7'S)-N⁴-benzoyl-1-(4'-hydroxy-3'-hydroxymethyl-1'-phenyl-2',6'-dioxabicyclo[3.3.0]oct-7'-yl)cytosine

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