benzyl (R)-citronellyl 3-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate

Base Information

• Chemical Name: benzyl (R)-citronellyl 3-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate
• CAS No.: 1352575-78-0
• Molecular Formula: C₂₈H₄₄NO₉P
• Molecular Weight: 569.632

Synonyms:benzyl (R)-citronellyl 3-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate

Chemical Property of benzyl (R)-citronellyl 3-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate

Chemical Property:

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Technology Process of benzyl (R)-citronellyl 3-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate

There total 8 articles about benzyl (R)-citronellyl 3-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate 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%

benzyl (R)-citronellyl 3-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate (1352575-70-2) → benzyl (R)-citronellyl 3-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate (1352575-78-0)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; water; at 0 - 20 ℃; for 6h; Inert atmosphere;

DOI:10.1039/c1ob06124k

Reference yield:

methyl 2-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)acetate (1182275-44-0) → benzyl (R)-citronellyl 3-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate (1352575-78-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: 1,4-diaza-bicyclo[2.2.2]octane / toluene / 7 h / Reflux; Inert atmosphere

2.2: DOWEX H⁺ (50WX₈-100) ion exchange resin / Inert atmosphere

3.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / tetrahydrofuran; water / 6 h / 0 - 20 °C / Inert atmosphere

With 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium; di-isopropyl azodicarboxylate; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; water; toluene; 3.1: Mitsunobu reaction;

DOI:10.1039/c1ob06124k

Reference yield:

3-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)prop-1-ene (1182275-42-8) → benzyl (R)-citronellyl 3-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate (1352575-78-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: ozone; sodium hydroxide / methanol; dichloromethane / 3 h / -78 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: 1,4-diaza-bicyclo[2.2.2]octane / toluene / 7 h / Reflux; Inert atmosphere

3.2: DOWEX H⁺ (50WX₈-100) ion exchange resin / Inert atmosphere

4.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

5.1: trifluoroacetic acid / tetrahydrofuran; water / 6 h / 0 - 20 °C / Inert atmosphere

With 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium; di-isopropyl azodicarboxylate; ozone; triphenylphosphine; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 4.1: Mitsunobu reaction;

DOI:10.1039/c1ob06124k

upstream raw materials:

3-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)propene

methyl 2-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)acetate

dibenzyl 3-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate

benzyl 3-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate

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