diethyl (1S,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropyl-phosphonate

Base Information

• Chemical Name: diethyl (1S,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropyl-phosphonate
• CAS No.: 150993-42-3
• Molecular Formula: C₂₇H₃₄NO₄P
• Molecular Weight: 467.545

Synonyms:diethyl (1S,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropyl-phosphonate

Chemical Property of diethyl (1S,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropyl-phosphonate

Chemical Property:

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Technology Process of diethyl (1S,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropyl-phosphonate

There total 9 articles about diethyl (1S,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropyl-phosphonate 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: 56.0%

diethyl phosphite lithium salt (72726-66-0) + (2S)-N,N-dibenzylphenylalaninal (123054-12-6,123808-74-2,136370-73-5,111060-64-1) → diethyl (1S,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropyl-phosphonate (150993-42-3) + diethyl (1R,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropyl-phosphonate (150993-41-2)

Guidance literature:

In tetrahydrofuran; at -30 - 20 ℃; diastereoselective reaction;

DOI:10.1002/ejoc.201800631

Reference yield: 50.0%

(2S)-N,N-dibenzylphenylalaninal (123054-12-6,123808-74-2,136370-73-5,111060-64-1) + phosphonic acid diethyl ester (762-04-9) → diethyl (1S,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropyl-phosphonate (150993-42-3) + diethyl (1R,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropyl-phosphonate (150993-41-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 20 ℃;

DOI:10.1007/s11176-005-0524-3

Reference yield:

lithium diethyl phosphite + (2S)-N,N-dibenzylphenylalaninal (123054-12-6,123808-74-2,136370-73-5,111060-64-1) → diethyl (1S,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropyl-phosphonate (150993-42-3) + diethyl (1R,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropyl-phosphonate (150993-41-2)

Guidance literature:

lithium diethyl phosphite; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; pentane; at -78 - 20 ℃; for 0.916667h; Inert atmosphere;

(2S)-N,N-dibenzylphenylalaninal; In tetrahydrofuran; pentane; at -30 - 20 ℃;

DOI:10.1016/j.jfluchem.2012.03.016

upstream raw materials:

(2S)-N,N-dibenzylphenylalaninal

phosphonic acid diethyl ester

L-phenylalanine

benzyl bromide

Downstream raw materials:

((1S,2S)-2-Amino-1-hydroxy-3-phenyl-propyl)-phosphonic acid diethyl ester

(1S,2S)-2-(dibenzylamino)-1-hydroxy-3-phenylpropylphosphonic acid

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