Acetic acid (1R,2R)-2-acetoxy-2-benzyloxycarbamoyl-1-(bis-benzyloxy-phosphoryloxymethyl)-ethyl ester

Base Information

• Chemical Name: Acetic acid (1R,2R)-2-acetoxy-2-benzyloxycarbamoyl-1-(bis-benzyloxy-phosphoryloxymethyl)-ethyl ester
• CAS No.: 717920-99-5
• Molecular Formula: C₂₉H₃₂NO₁₀P
• Molecular Weight: 585.548
• Mol file: 717920-99-5.mol

Synonyms:Acetic acid (1R,2R)-2-acetoxy-2-benzyloxycarbamoyl-1-(bis-benzyloxy-phosphoryloxymethyl)-ethyl ester

Chemical Property of Acetic acid (1R,2R)-2-acetoxy-2-benzyloxycarbamoyl-1-(bis-benzyloxy-phosphoryloxymethyl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1R,2R)-2-acetoxy-2-benzyloxycarbamoyl-1-(bis-benzyloxy-phosphoryloxymethyl)-ethyl ester

There total 4 articles about Acetic acid (1R,2R)-2-acetoxy-2-benzyloxycarbamoyl-1-(bis-benzyloxy-phosphoryloxymethyl)-ethyl ester 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: 58.0%

acetic anhydride (108-24-7) + Phosphoric acid dibenzyl ester (2R,3R)-3-benzyloxycarbamoyl-2,3-dihydroxy-propyl ester (717920-98-4) → Acetic acid (1R,2R)-2-acetoxy-2-benzyloxycarbamoyl-1-(bis-benzyloxy-phosphoryloxymethyl)-ethyl ester (717920-99-5)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 15h;

DOI:10.1021/jm031066i

Reference yield: 22.0%

acetic anhydride (108-24-7) + Phosphoric acid dibenzyl ester (2R,3R)-3-benzyloxycarbamoyl-2,3-dihydroxy-propyl ester (717920-98-4) → Acetic acid (1R,2R)-2-acetoxy-2-benzyloxycarbamoyl-1-(bis-benzyloxy-phosphoryloxymethyl)-ethyl ester (717920-99-5) + Acetic acid (1R,2R)-2-acetoxy-3-(acetyl-benzyloxy-amino)-1-(bis-benzyloxy-phosphoryloxymethyl)-3-oxo-propyl ester

Guidance literature:

With pyridine; dmap; at 20 ℃;

DOI:10.1021/jm031066i

Reference yield:

(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-N-(phenylmethoxy)-1,3-dioxolane-4-carboxamide (717920-96-2) → Acetic acid (1R,2R)-2-acetoxy-2-benzyloxycarbamoyl-1-(bis-benzyloxy-phosphoryloxymethyl)-ethyl ester (717920-99-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / pyridine / CH₂Cl₂ / 1.5 h / -78 °C

2: 57 percent / Dowex 50WX₈-200 resin / methanol; H₂O / 48 h / 20 °C

3: 58 percent / DMAP; pyridine / 15 h / 20 °C

With pyridine; dmap; Dowex 50wx8-200 resin; In methanol; dichloromethane; water;

DOI:10.1021/jm031066i

upstream raw materials:

acetic anhydride

Phosphoric acid dibenzyl ester (2R,3R)-3-benzyloxycarbamoyl-2,3-dihydroxy-propyl ester

(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-N-(phenylmethoxy)-1,3-dioxolane-4-carboxamide

Phosphoric acid dibenzyl ester (4R,5R)-5-benzyloxycarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester