6-(N³-benzoylthymine-1-yl)-1-O-(2-benzyloxyethyl)-2-deoxy-2-phthalimino-β-D-glucopyranoside

Base Information

• Chemical Name: 6-(N³-benzoylthymine-1-yl)-1-O-(2-benzyloxyethyl)-2-deoxy-2-phthalimino-β-D-glucopyranoside
• CAS No.: 1447811-21-3
• Molecular Formula: C₃₅H₃₃N₃O₁₀
• Molecular Weight: 655.661

Synonyms:6-(N³-benzoylthymine-1-yl)-1-O-(2-benzyloxyethyl)-2-deoxy-2-phthalimino-β-D-glucopyranoside

Chemical Property of 6-(N³-benzoylthymine-1-yl)-1-O-(2-benzyloxyethyl)-2-deoxy-2-phthalimino-β-D-glucopyranoside

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Technology Process of 6-(N³-benzoylthymine-1-yl)-1-O-(2-benzyloxyethyl)-2-deoxy-2-phthalimino-β-D-glucopyranoside

There total 1 articles about 6-(N³-benzoylthymine-1-yl)-1-O-(2-benzyloxyethyl)-2-deoxy-2-phthalimino-β-D-glucopyranoside 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: 84.0%

1-O-(2-benzyloxyethyl)-2-deoxy-2-phthalimino-β-D-glucopyranoside (1261030-96-9) + 3-N-benzoyluracil (2775-87-3) → 6-(N3-benzoylthymine-1-yl)-1-O-(2-benzyloxyethyl)-2-deoxy-2-phthalimino-β-D-glucopyranoside (1447811-21-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1016/j.bmcl.2013.05.036

Reference yield: 87.0%

6-(N3-benzoylthymine-1-yl)-1-O-(2-benzyloxyethyl)-2-deoxy-2-phthalimino-β-D-glucopyranoside (1447811-21-3) → 2-amino-1-O-(2-benzyloxyethyl)-2-deoxy-6-(thymine-1-yl)-β-D-glucopyranoside (1447811-22-4)

Guidance literature:

With ethylenediamine; In ethanol; for 2h; Inert atmosphere; Reflux;

DOI:10.1016/j.bmcl.2013.05.036

Reference yield:

6-(N3-benzoylthymine-1-yl)-1-O-(2-benzyloxyethyl)-2-deoxy-2-phthalimino-β-D-glucopyranoside (1447811-21-3) → 1-O-(2-benzyloxyethyl)-2-deoxy-6-(thymine-1-yl)-2-trifluoroacetylamino-β-D-glucopyranoside (1447811-23-5)

Guidance literature:

Multi-step reaction with 2 steps

1: ethylenediamine / ethanol / 2 h / Inert atmosphere; Reflux

2: pyridine / 0 - 20 °C / Inert atmosphere

With pyridine; ethylenediamine; In ethanol;

DOI:10.1016/j.bmcl.2013.05.036

upstream raw materials:

1-O-(2-benzyloxyethyl)-2-deoxy-2-phthalimino-β-D-glucopyranoside

3-N-benzoyluracil

Downstream raw materials:

2-amino-1-O-(2-benzyloxyethyl)-2-deoxy-6-(thymine-1-yl)-β-D-glucopyranoside

1-O-(2-benzyloxyethyl)-2-deoxy-6-(thymine-1-yl)-2-trifluoroacetylamino-β-D-glucopyranoside

2-deoxy-1-O-[2-(4,4'-dimethoxytrityloxy)ethyl]-6-(thymine-1-yl)-2-trifluoroacetylamino-β-D-glucopyranoside

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