dimethyl C-(2'-acetamido-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) methylphosphonate

Base Information

• Chemical Name: dimethyl C-(2'-acetamido-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) methylphosphonate
• CAS No.: 667917-63-7
• Molecular Formula: C₃₂H₄₀NO₉P
• Molecular Weight: 613.645

Synonyms:dimethyl C-(2'-acetamido-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) methylphosphonate

Chemical Property of dimethyl C-(2'-acetamido-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) methylphosphonate

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Technology Process of dimethyl C-(2'-acetamido-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) methylphosphonate

There total 2 articles about dimethyl C-(2'-acetamido-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) methylphosphonate 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: 96.0%

2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucono-1,5-lacton (34051-37-1) + dimethyl lithiomethylphosphonate (34939-91-8,58648-56-9) → dimethyl C-(2'-acetamido-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) methylphosphonate (667917-63-7)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1016/j.tetlet.2003.12.081

Reference yield: 56.0%

2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucono-1,5-lacton (34051-37-1) + dimethyl methane phosphonate (756-79-6) → dimethyl C-(2'-acetamido-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) methylphosphonate (667917-63-7)

Guidance literature:

dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -80 ℃; for 0.25h;

2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucono-1,5-lacton; In tetrahydrofuran; hexane; at -80 ℃; for 0.833333h;

DOI:10.1021/jo0353029

Reference yield: 70.0%

dimethyl C-(2'-acetamido-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl) methylphosphonate (667917-63-7) → (Z)-3-acetamido-2,6-annhydro-4,5,7-tri-O-benzyl-1,3-dideoxy-1-dimethoxyphosphoryl-D-gluco-hept-1-enitol (667917-65-9)

Guidance literature:

With sodium acetate; acetic anhydride; at 100 ℃; for 2h;

DOI:10.1016/j.tetlet.2003.12.081

upstream raw materials:

2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucono-1,5-lacton

dimethyl lithiomethylphosphonate

dimethyl methane phosphonate

Downstream raw materials:

(Z)-3-acetamido-2,6-annhydro-4,5,7-tri-O-benzyl-1,3-dideoxy-1-dimethoxyphosphoryl-D-gluco-hept-1-enitol

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