(3S,5S,6R)-3-(3-Iodo-propyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

Base Information

• Chemical Name: (3S,5S,6R)-3-(3-Iodo-propyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester
• CAS No.: 144542-62-1
• Molecular Formula: C₂₇H₂₆INO₄
• Molecular Weight: 555.412
• Mol file: 144542-62-1.mol

Synonyms:(3S,5S,6R)-3-(3-Iodo-propyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

Chemical Property of (3S,5S,6R)-3-(3-Iodo-propyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S,6R)-3-(3-Iodo-propyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

There total 2 articles about (3S,5S,6R)-3-(3-Iodo-propyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester 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: 89.0%

(3S,5S,6R)-3-(3-Chloro-propyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (144542-63-2) → (3S,5S,6R)-3-(3-Iodo-propyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (144542-62-1)

Guidance literature:

With sodium iodide; In acetone; Heating;

DOI:10.1021/jo00050a028

Reference yield:

(5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (100516-54-9,335159-14-3) → (3S,5S,6R)-3-(3-Iodo-propyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (144542-62-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 51.6 percent / NaN(SiMe₃)2, 15-crown-5 / tetrahydrofuran; hexamethylphosphoric acid triamide; CH₂Cl₂ / 1) -78 deg C, 10 min, 2) -78 deg C to rt, 2 h

2: 89 percent / NaI / acetone / Heating

With 15-crown-5; sodium hexamethyldisilazane; sodium iodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; acetone;

DOI:10.1021/jo00050a028

Reference yield:

(3S,5S,6R)-3-(3-Iodo-propyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (144542-62-1) → (S,S)-2,6-diaminopimelic acid (14289-34-0,1356383-43-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) NaN(SiMe₃)2, 15-crown-5 / 1) THF/HMPA/CH₂Cl₂, -78 deg C, 10 min, 2) -78 deg C, 2 h

2: 1) H₂, 2) propylene oxide / 1) PdCl₂ / 1) EtOH/CH₂Cl₂, 60 psi, 48 h, 2) EtOH, reflux, 30 min

With 15-crown-5; hydrogen; sodium hexamethyldisilazane; methyloxirane; palladium dichloride;

DOI:10.1021/jo00050a028

upstream raw materials:

(3S,5S,6R)-3-(3-Chloro-propyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

(5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Downstream raw materials:

(S,S)-2,6-diaminopimelic acid