2-((2S,3S,5R)-3-Azido-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-4-methoxy-5-methyl-pyrimidine

Base Information

• Chemical Name: 2-((2S,3S,5R)-3-Azido-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-4-methoxy-5-methyl-pyrimidine
• CAS No.: 155446-90-5
• Molecular Formula: C₁₇H₁₉N₅O₃S
• Molecular Weight: 373.436

Synonyms:2-((2S,3S,5R)-3-Azido-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-4-methoxy-5-methyl-pyrimidine

Chemical Property of 2-((2S,3S,5R)-3-Azido-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-4-methoxy-5-methyl-pyrimidine

Chemical Property:

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Technology Process of 2-((2S,3S,5R)-3-Azido-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-4-methoxy-5-methyl-pyrimidine

There total 2 articles about 2-((2S,3S,5R)-3-Azido-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-4-methoxy-5-methyl-pyrimidine 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: 81.0%

2‐chloro‐4‐methoxy‐5‐methylpyrimidine (135292-35-2) + ((2S,3S,5R)-3-Azido-5-phenylsulfanyl-tetrahydro-furan-2-yl)-methanol → 2-((2S,3S,5R)-3-Azido-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-4-methoxy-5-methyl-pyrimidine (155446-90-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at -50 ℃;

DOI:10.1016/S0040-4039(00)73186-8

Reference yield: 34.0%

2‐chloro‐4‐methoxy‐5‐methylpyrimidine (135292-35-2) + ((2S,3S,5R)-3-Azido-5-phenylsulfanyl-tetrahydro-furan-2-yl)-methanol → 2-((2S,3S,5R)-3-Azido-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-4-methoxy-5-methyl-pyrimidine (155446-90-5) + 4-Methoxy-5-methyl-2-((2S,5R)-5-phenylsulfanyl-2,5-dihydro-furan-2-ylmethoxy)-pyrimidine

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 1h; Ambient temperature;

DOI:10.1039/c39940002541

Reference yield:

2-((2S,3S,5R)-3-Azido-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-4-methoxy-5-methyl-pyrimidine (155446-90-5) → 3'-azido-2',3'-deoxythymidine (30516-87-1,399024-19-2)

Guidance literature:

Multi-step reaction with 3 steps

1: dimethyl(methylthio)sulfonium tetrafluoroborate, MS 4A / acetonitrile / -20 °C

2: 1 M NaOH / acetonitrile / 0 °C

3: Dowex 50 / ethanol; H₂O

With sodium hydroxide; Dowex 50; dimethyl(methylthio)sulfonium tetrafluoroborate; In ethanol; water; acetonitrile;

DOI:10.1016/S0040-4039(00)73186-8

upstream raw materials:

2‐chloro‐4‐methoxy‐5‐methylpyrimidine

Downstream raw materials:

3'-azido-2',3'-deoxythymidine

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