dibenzyl (1R,2S)-1,2-epoxypropylphosphonate

Base Information

• Chemical Name: dibenzyl (1R,2S)-1,2-epoxypropylphosphonate
• CAS No.: 172585-28-3
• Molecular Formula: C₁₇H₁₉O₄P
• Molecular Weight: 318.309
• Mol file: 172585-28-3.mol

Synonyms:dibenzyl (1R,2S)-1,2-epoxypropylphosphonate

Chemical Property of dibenzyl (1R,2S)-1,2-epoxypropylphosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of dibenzyl (1R,2S)-1,2-epoxypropylphosphonate

There total 4 articles about dibenzyl (1R,2S)-1,2-epoxypropylphosphonate 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: 77.0%

Methanesulfonic acid (1S,2S)-1-(bis-benzyloxy-phosphoryl)-2-triisopropylsilanyloxy-propyl ester → dibenzyl (1R,2S)-1,2-epoxypropylphosphonate (172585-28-3)

Guidance literature:

With tetrabutyl ammonium fluoride; silica gel; In tetrahydrofuran; for 8h; Ambient temperature;

DOI:10.1016/0957-4166(95)00281-S

Reference yield: 58.0%

Dibenzyl phosphite (17176-77-1) + (R)-1-formylethyl p-toluenesulfonate (38195-12-9) → dibenzyl (1S,2S)-1,2-epoxypropylphosphonate (1015479-72-7) + dibenzyl (1R,2S)-1,2-epoxypropylphosphonate (172585-28-3)

Guidance literature:

Dibenzyl phosphite; (R)-1-formylethyl p-toluenesulfonate; With titanium(IV) isopropylate; In dichloromethane; at -5 ℃; for 10h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 3h; Further stages.;

DOI:10.3987/com-07-s(w)45

Reference yield:

4-Nitro-benzenesulfonic acid (1S,2S)-1-(bis-benzyloxy-phosphoryl)-2-hydroxy-propyl ester → dibenzyl (1R,2S)-1,2-epoxypropylphosphonate (172585-28-3)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 30h;

DOI:10.1021/jo010701u

upstream raw materials:

dibenzyl (1S,2S)-1,2-dihydroxypropylphosphonate

Dibenzyl phosphite

(R)-1-formylethyl p-toluenesulfonate

Downstream raw materials:

phosphomycin disodium salt

Refernces

• 1、 Kobayashi,William,Tokoro. "Sharpless asymmetric dihydroxylation of trans-propenylphosphonate by using a modified AD-mix-α and the synthesis of fosfomycin". . p. 7903 - 7906. Retrieved 2007/10/03.