Acetic acid (1R,2S,3R,5S,6R)-2-acetoxy-3,5-diazido-6-(4-oxo-3,4-dihydro-quinazolin-2-ylsulfanylmethoxy)-cyclohexyl ester

Base Information

• Chemical Name: Acetic acid (1R,2S,3R,5S,6R)-2-acetoxy-3,5-diazido-6-(4-oxo-3,4-dihydro-quinazolin-2-ylsulfanylmethoxy)-cyclohexyl ester
• CAS No.: 609342-53-2
• Molecular Formula: C₁₉H₂₀N₈O₆S
• Molecular Weight: 488.484

Synonyms:Acetic acid (1R,2S,3R,5S,6R)-2-acetoxy-3,5-diazido-6-(4-oxo-3,4-dihydro-quinazolin-2-ylsulfanylmethoxy)-cyclohexyl ester

Chemical Property of Acetic acid (1R,2S,3R,5S,6R)-2-acetoxy-3,5-diazido-6-(4-oxo-3,4-dihydro-quinazolin-2-ylsulfanylmethoxy)-cyclohexyl ester

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Technology Process of Acetic acid (1R,2S,3R,5S,6R)-2-acetoxy-3,5-diazido-6-(4-oxo-3,4-dihydro-quinazolin-2-ylsulfanylmethoxy)-cyclohexyl ester

There total 2 articles about Acetic acid (1R,2S,3R,5S,6R)-2-acetoxy-3,5-diazido-6-(4-oxo-3,4-dihydro-quinazolin-2-ylsulfanylmethoxy)-cyclohexyl ester 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:

Acetic acid (1R,2S,3R,5S,6R)-2-acetoxy-3,5-diazido-6-methylsulfanylmethoxy-cyclohexyl ester (609342-42-9) → Acetic acid (1R,2S,3R,5S,6R)-2-acetoxy-3,5-diazido-6-(4-oxo-3,4-dihydro-quinazolin-2-ylsulfanylmethoxy)-cyclohexyl ester (609342-53-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / SO₂Cl₂ / CH₂Cl₂ / 0.5 h / 20 °C

2: NaH / acetonitrile; dimethylformamide

With sulfuryl dichloride; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/anie.200351354

Reference yield:

2-mercapto-3H-quinazolin-4-one (13906-09-7) + Acetic acid (1S,2R,3R,4S,6R)-2-acetoxy-4,6-diazido-3-chloromethoxy-cyclohexyl ester (609342-43-0) → Acetic acid (1R,2S,3R,5S,6R)-2-acetoxy-3,5-diazido-6-(4-oxo-3,4-dihydro-quinazolin-2-ylsulfanylmethoxy)-cyclohexyl ester (609342-53-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/anie.200351354

Reference yield:

Acetic acid (1R,2S,3R,5S,6R)-2-acetoxy-3,5-diazido-6-(4-oxo-3,4-dihydro-quinazolin-2-ylsulfanylmethoxy)-cyclohexyl ester (609342-53-2) → 2-((1R,2R,3S,4R,6S)-4,6-Diazido-2,3-dihydroxy-cyclohexyloxymethylsulfanyl)-3H-quinazolin-4-one

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 4h;

DOI:10.1002/anie.200351354

upstream raw materials:

2-mercapto-3H-quinazolin-4-one

Acetic acid (1S,2R,3R,4S,6R)-2-acetoxy-4,6-diazido-3-chloromethoxy-cyclohexyl ester

Acetic acid (1R,2S,3R,5S,6R)-2-acetoxy-3,5-diazido-6-methylsulfanylmethoxy-cyclohexyl ester

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