(3R,5S)-5-[(tert-butoxycarbonyl)amino]-2-ethoxy-3-phenyl-2-oxo-1,2-oxaphosphorinane

Base Information

• Chemical Name: (3R,5S)-5-[(tert-butoxycarbonyl)amino]-2-ethoxy-3-phenyl-2-oxo-1,2-oxaphosphorinane
• CAS No.: 618893-58-6
• Molecular Formula: C₁₇H₂₆NO₅P
• Molecular Weight: 355.371
• Mol file: 618893-58-6.mol

Synonyms:(3R,5S)-5-[(tert-butoxycarbonyl)amino]-2-ethoxy-3-phenyl-2-oxo-1,2-oxaphosphorinane

Chemical Property of (3R,5S)-5-[(tert-butoxycarbonyl)amino]-2-ethoxy-3-phenyl-2-oxo-1,2-oxaphosphorinane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S)-5-[(tert-butoxycarbonyl)amino]-2-ethoxy-3-phenyl-2-oxo-1,2-oxaphosphorinane

There total 8 articles about (3R,5S)-5-[(tert-butoxycarbonyl)amino]-2-ethoxy-3-phenyl-2-oxo-1,2-oxaphosphorinane 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: 67.0%

ethyl (2S,4R)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-4-phenylbutanoate (618893-41-7) → (3R,5S)-5-[(tert-butoxycarbonyl)amino]-2-ethoxy-3-phenyl-2-oxo-1,2-oxaphosphorinane (618893-58-6) + (1R,3S)-(3-[(tert-butoxycarbonyl)amino]-4-hydroxy-1-phenylbutyl)phosphonic acid diethyl ester

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 0 - 20 ℃; for 96h;

DOI:10.1021/jo034707q

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (3R,5S)-5-[(tert-butoxycarbonyl)amino]-2-ethoxy-3-phenyl-2-oxo-1,2-oxaphosphorinane (618893-58-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / Na₂CO₃; NaHCO₃ / dioxane; H₂O / 7 h / 0 - 20 °C

2: 27 percent / LiBH₄ / tetrahydrofuran / 96 h / 0 - 20 °C

With lithium borohydride; sodium hydrogencarbonate; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1021/jo034707q

Reference yield:

ethyl (2S,4S)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-4-phenylbutanoate (618893-49-5) → (3R,5S)-5-[(tert-butoxycarbonyl)amino]-2-ethoxy-3-phenyl-2-oxo-1,2-oxaphosphorinane (618893-58-6)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0957-4166(02)00082-4

upstream raw materials:

ethyl (2S,4S)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-4-phenylbutanoate

ethyl (2S,4R)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-4-phenylbutanoate

di-tert-butyl dicarbonate

O,O-diethyl benzylphosphonate