dibenzylphosphate-2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside

Base Information

• Chemical Name: dibenzylphosphate-2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside
• CAS No.: 949007-44-7
• Molecular Formula: C₃₆H₃₅FNO₁₀P
• Molecular Weight: 691.647
• Mol file: 949007-44-7.mol

Synonyms:dibenzylphosphate-2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside

Chemical Property of dibenzylphosphate-2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dibenzylphosphate-2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside

There total 7 articles about dibenzylphosphate-2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-α-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: 89.0%

2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-D-glucopyranose + dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate (990-91-0) → dibenzylphosphate-2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside (949007-44-7)

Guidance literature:

2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-D-glucopyranose; With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; at -78 ℃; for 0.25h;

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate; In tetrahydrofuran; n-heptane; ethylbenzene; at 0 ℃; for 3h; Further stages.;

DOI:10.1016/j.tetasy.2007.05.032

Reference yield:

allyl 2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside (946495-23-4) → dibenzylphosphate-2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside (949007-44-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 79 percent / AcOH / tetrakis(triphenylphosphine)palladium / 2 h / 80 °C

2.1: LDA / tetrahydrofuran; heptane; ethylbenzene / 0.25 h / -78 °C

2.2: 89 percent / tetrahydrofuran; heptane; ethylbenzene / 3 h / 0 °C

With acetic acid; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; n-heptane; ethylbenzene;

DOI:10.1016/j.tetasy.2007.05.032

Reference yield:

benzyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-galactopyranoside (868744-51-8) → dibenzylphosphate-2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside (949007-44-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diethylamino-sulfur trifluoride / dichloromethane / 2 h / -40 - 20 °C

2.1: iron(III) chloride / dichloromethane / 3 h / 20 °C / Inert atmosphere

3.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C

3.2: 3.5 h / -78 - 0 °C

With iron(III) chloride; diethylamino-sulfur trifluoride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/acs.joc.6b02929

upstream raw materials:

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

allyl 2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside

(3R,4R,5R,6R)-3-acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate

benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside