dibenzyl 1-phenyl-3-hydroxy-4-(p-toluenesulfonyloxy)butanephosphonate

Base Information

• Chemical Name: dibenzyl 1-phenyl-3-hydroxy-4-(p-toluenesulfonyloxy)butanephosphonate
• CAS No.: 887232-62-4
• Molecular Formula: C₃₁H₃₃O₇PS
• Molecular Weight: 580.639
• Mol file: 887232-62-4.mol

Synonyms:dibenzyl 1-phenyl-3-hydroxy-4-(p-toluenesulfonyloxy)butanephosphonate

Chemical Property of dibenzyl 1-phenyl-3-hydroxy-4-(p-toluenesulfonyloxy)butanephosphonate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of dibenzyl 1-phenyl-3-hydroxy-4-(p-toluenesulfonyloxy)butanephosphonate

There total 1 articles about dibenzyl 1-phenyl-3-hydroxy-4-(p-toluenesulfonyloxy)butanephosphonate 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:

glycidyl p-toluenesulfonate (118712-54-2,6746-81-2) + benzyl-phosphonic acid dibenzyl ester (82180-48-1) → dibenzyl 1-phenyl-3-hydroxy-4-(p-toluenesulfonyloxy)butanephosphonate (887232-62-4)

Guidance literature:

benzyl-phosphonic acid dibenzyl ester; With n-butyllithium; In tetrahydrofuran; hexane; at -70 ℃; for 0.25h;

glycidyl p-toluenesulfonate; With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 7h;

DOI:10.1021/jm051177c

Reference yield: 89.0%

dibenzyl 1-phenyl-3-hydroxy-4-(p-toluenesulfonyloxy)butanephosphonate (887232-62-4) → dibenzyl 1-phenyl-3,4-epoxybutanephosphonate (887232-55-5)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1021/jm051177c

Reference yield:

dibenzyl 1-phenyl-3-hydroxy-4-(p-toluenesulfonyloxy)butanephosphonate (887232-62-4) → 2-[N-(acetyl),N-(hydroxy)aminomethyl]-1-phenylcyclopropylphosphonate

Guidance literature:

Multi-step reaction with 7 steps

1.1: 89 percent / t-BuOK / tetrahydrofuran / 3 h / 0 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C

2.2: 52 percent / BF₃*OEt₂ / hexane; tetrahydrofuran / 0.25 h / -78 °C

3.1: 74 percent / Et₃N; Me₃N*HCl / CH₂Cl₂ / 1 h / 0 °C

4.1: NaH / dimethylformamide / 0.5 h / 20 °C

4.2: 90 percent / dimethylformamide / 3 h / 50 °C

5.1: 100 percent / TFA / CH₂Cl₂ / 0.75 h / 0 °C

6.1: pyridine / 20 °C

7.1: H₂ / Pd/C / methanol / 20 °C / 760 Torr

With pyridine; n-butyllithium; potassium tert-butylate; hydrogen; trimethylamine hydrochloride; sodium hydride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm051177c

upstream raw materials:

glycidyl p-toluenesulfonate

benzyl-phosphonic acid dibenzyl ester

Downstream raw materials:

dibenzyl 1-phenyl-3,4-epoxybutanephosphonate