dimethyl (1S,2S)-1-acetyloxy-3-azido-2-benzyloxypropylphosphonate

Base Information

• Chemical Name: dimethyl (1S,2S)-1-acetyloxy-3-azido-2-benzyloxypropylphosphonate
• CAS No.: 464203-96-1
• Molecular Formula: C₁₄H₂₀N₃O₆P
• Molecular Weight: 357.303
• Mol file: 464203-96-1.mol

Synonyms:dimethyl (1S,2S)-1-acetyloxy-3-azido-2-benzyloxypropylphosphonate

Chemical Property of dimethyl (1S,2S)-1-acetyloxy-3-azido-2-benzyloxypropylphosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl (1S,2S)-1-acetyloxy-3-azido-2-benzyloxypropylphosphonate

There total 7 articles about dimethyl (1S,2S)-1-acetyloxy-3-azido-2-benzyloxypropylphosphonate 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: 92.0%

acetic anhydride (108-24-7) + dimethyl (1S,2S)-3-azido-2-benzyloxy-1-hydroxypropylphosphonate (464203-92-7) → dimethyl (1S,2S)-1-acetyloxy-3-azido-2-benzyloxypropylphosphonate (464203-96-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/S0957-4166(02)00223-9

Reference yield:

benzyl bromide (100-39-0) → dimethyl (1S,2S)-1-acetyloxy-3-azido-2-benzyloxypropylphosphonate (464203-96-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 72 percent / Ag₂O; molecular sieves / 4 h / 20 °C

2: 90 percent / LiCl; NaBH₄ / tetrahydrofuran; ethanol / 20 h / 0 - 20 °C

3: 99 percent / pyridine / CH₂Cl₂ / 20 h / 20 °C

4: 81 percent / NaN₃ / dimethylformamide / 48 h / 60 °C

5: 93 percent / H₅IO₆ / ethyl acetate / 1 h / 20 °C

6: 43 percent / Et₃N / 20 h / 20 °C

7: 92 percent / Et₃N; DMAP / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; sodium azide; molecular sieve; periodic acid; triethylamine; lithium chloride; silver(l) oxide; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(02)00223-9

Reference yield:

2-O-benzyl-3,4-O-isopropylidene-L-threitol (84379-53-3) → dimethyl (1S,2S)-1-acetyloxy-3-azido-2-benzyloxypropylphosphonate (464203-96-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / pyridine / CH₂Cl₂ / 20 h / 20 °C

2: 81 percent / NaN₃ / dimethylformamide / 48 h / 60 °C

3: 93 percent / H₅IO₆ / ethyl acetate / 1 h / 20 °C

4: 43 percent / Et₃N / 20 h / 20 °C

5: 92 percent / Et₃N; DMAP / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; dmap; sodium azide; periodic acid; triethylamine; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(02)00223-9

upstream raw materials:

acetic anhydride

dimethyl (1S,2S)-3-azido-2-benzyloxy-1-hydroxypropylphosphonate

benzyl bromide

2-O-benzyl-3,4-O-isopropylidene-L-threitol