5-Chloro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-phenylsulfanyl-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 5-Chloro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-phenylsulfanyl-1H-pyrimidine-2,4-dione
• CAS No.: 87817-97-8
• Molecular Formula: C₂₀H₂₃ClN₂O₇S
• Molecular Weight: 470.931

Synonyms:5-Chloro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-phenylsulfanyl-1H-pyrimidine-2,4-dione

Chemical Property of 5-Chloro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-phenylsulfanyl-1H-pyrimidine-2,4-dione

Chemical Property:

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Technology Process of 5-Chloro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-phenylsulfanyl-1H-pyrimidine-2,4-dione

There total 2 articles about 5-Chloro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-phenylsulfanyl-1H-pyrimidine-2,4-dione 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: 91.0%

5-Chloro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione (87817-92-3) + diphenyldisulfane (882-33-7) → 5-Chloro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-phenylsulfanyl-1H-pyrimidine-2,4-dione (87817-97-8)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -70 ℃;

DOI:10.1248/cpb.31.2164

Reference yield:

2',3'-O-isopropylidene-5-chlorouridine (81356-82-3) → 5-Chloro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-phenylsulfanyl-1H-pyrimidine-2,4-dione (87817-97-8)

Guidance literature:

Multi-step reaction with 2 steps

1: methanesulfonic acid / acetone

2: 91 percent / LDA / tetrahydrofuran / -70 °C

With methanesulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; acetone;

DOI:10.1248/cpb.31.2164

Reference yield: 79.0%

5-Chloro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-phenylsulfanyl-1H-pyrimidine-2,4-dione (87817-97-8) → 5-Chloro-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-phenylsulfanyl-1H-pyrimidine-2,4-dione (87818-07-3)

Guidance literature:

With trifluoroacetic acid; Ambient temperature;

DOI:10.1248/cpb.31.2164

upstream raw materials:

5-Chloro-1-((3aR,4R,6R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione

diphenyldisulfane

2',3'-O-isopropylidene-5-chlorouridine

Downstream raw materials:

5-Chloro-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-phenylsulfanyl-1H-pyrimidine-2,4-dione

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