(2S,3S,4S,5R,6R)-6-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-3-azido-4,5-bis-benzoyloxy-tetrahydro-pyran-2-carboxylic acid

Base Information

• Chemical Name: (2S,3S,4S,5R,6R)-6-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-3-azido-4,5-bis-benzoyloxy-tetrahydro-pyran-2-carboxylic acid
• CAS No.: 575457-74-8
• Molecular Formula: C₂₄H₂₀N₆O₈
• Molecular Weight: 520.458

Synonyms:(2S,3S,4S,5R,6R)-6-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-3-azido-4,5-bis-benzoyloxy-tetrahydro-pyran-2-carboxylic acid

Chemical Property of (2S,3S,4S,5R,6R)-6-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-3-azido-4,5-bis-benzoyloxy-tetrahydro-pyran-2-carboxylic acid

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Technology Process of (2S,3S,4S,5R,6R)-6-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-3-azido-4,5-bis-benzoyloxy-tetrahydro-pyran-2-carboxylic acid

There total 2 articles about (2S,3S,4S,5R,6R)-6-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-3-azido-4,5-bis-benzoyloxy-tetrahydro-pyran-2-carboxylic acid 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:

4-amino-1-(4-azido-O2,O3-dibenzoyl-β-D-4-deoxy-glucopyranosyl)-1H-pyrimidin-2-one (35847-75-7) → (2S,3S,4S,5R,6R)-6-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-3-azido-4,5-bis-benzoyloxy-tetrahydro-pyran-2-carboxylic acid (575457-74-8)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; water; In acetonitrile; at 20 ℃; for 4h;

DOI:10.1021/ol0507322

Reference yield:

4-acetylamino-1-(O6-acetyl-4-azido-O2,O3-dibenzoyl-β-D-4-deoxy-glucopyranosyl)-1H-pyrimidin-2-one (35847-73-5) → (2S,3S,4S,5R,6R)-6-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-3-azido-4,5-bis-benzoyloxy-tetrahydro-pyran-2-carboxylic acid (575457-74-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / methanol / 48 h / 20 °C

2: 6.6 g / H₂O; TEMPO; iodobenzene diacetate / acetonitrile / 4 h / 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; water; triethylamine; In methanol; acetonitrile;

DOI:10.1021/ol0507322

Reference yield:

(2S,3S,4S,5R,6R)-6-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-3-azido-4,5-bis-benzoyloxy-tetrahydro-pyran-2-carboxylic acid (575457-74-8) + carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 2-(trimethylsilanyl)-ethyl ester (78269-85-9) → (2S,3S,4S,5R,6R)-3-Azido-4,5-bis-benzoyloxy-6-[2-oxo-4-(2-trimethylsilanyl-ethoxycarbonylamino)-2H-pyrimidin-1-yl]-tetrahydro-pyran-2-carboxylic acid (863871-04-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 65 ℃; for 48h;

DOI:10.1021/ol0507322

upstream raw materials:

4-amino-1-(4-azido-O²,O³-dibenzoyl-β-D-4-deoxy-glucopyranosyl)-1H-pyrimidin-2-one

4-acetylamino-1-(O⁶-acetyl-4-azido-O²,O³-dibenzoyl-β-D-4-deoxy-glucopyranosyl)-1H-pyrimidin-2-one

Downstream raw materials:

(2S,3S,4S,5R,6R)-3-Azido-4,5-bis-benzoyloxy-6-[2-oxo-4-(2-trimethylsilanyl-ethoxycarbonylamino)-2H-pyrimidin-1-yl]-tetrahydro-pyran-2-carboxylic acid

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