(2S)-2-benzyloxycarbonylamino-4-phenylselenyl-butyric acid methyl ester

Base Information

• Chemical Name: (2S)-2-benzyloxycarbonylamino-4-phenylselenyl-butyric acid methyl ester
• CAS No.: 104523-60-6
• Molecular Formula: C₁₉H₂₁NO₄Se
• Molecular Weight: 406.34
• Mol file: 104523-60-6.mol

Synonyms:(2S)-2-benzyloxycarbonylamino-4-phenylselenyl-butyric acid methyl ester

Chemical Property of (2S)-2-benzyloxycarbonylamino-4-phenylselenyl-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2-benzyloxycarbonylamino-4-phenylselenyl-butyric acid methyl ester

There total 3 articles about (2S)-2-benzyloxycarbonylamino-4-phenylselenyl-butyric acid methyl 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: 98.0%

diphenyl diselenide (1666-13-3) + (2S)-2-benzyloxycarbonylamino-4-bromo-butyric acid methyl ester (15159-67-8) → (2S)-2-benzyloxycarbonylamino-4-phenylselenyl-butyric acid methyl ester (104523-60-6)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 20 ℃;

DOI:10.1021/jo0507439

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (2S)-2-benzyloxycarbonylamino-4-phenylselenyl-butyric acid methyl ester (104523-60-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: SOCl₂ / 0 - 20 °C

1.2: 7.1 g / NaHCO₃ / CH₂Cl₂; H₂O / 0 - 20 °C

2.1: 98 percent / NaBH₄ / ethanol / 20 °C

With sodium tetrahydroborate; thionyl chloride; In ethanol;

DOI:10.1021/jo0507439

Reference yield:

Z-L-GluOMe (5672-83-3) → (2S)-2-benzyloxycarbonylamino-4-phenylselenyl-butyric acid methyl ester (104523-60-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) isobutylchloroformate, N-methylmorpholine, 2.) N-methylmorpholine, 3.) bromotrichloromethane / 1.) THF, -15 deg C, 15 min, 2.) THF, -15 deg C, 45 min, 3.) irrad, RT, 3 h

2: 1.) NaBH₄, 3.) HCl / 1.) EtOH, 0 deg C, 2.) EtOH, 0 deg C, 20 min

With 4-methyl-morpholine; hydrogenchloride; sodium tetrahydroborate; Bromotrichloromethane; isobutyl chloroformate;

DOI:10.1016/S0040-4020(01)97206-0

upstream raw materials:

diphenyl diselenide

(2S)-2-benzyloxycarbonylamino-4-bromo-butyric acid methyl ester

benzyl chloroformate

Z-L-GluOMe

Downstream raw materials:

(S)-2-benzyloxycarbonylamino-4-hydroxyphosphinoyl-butyric acid methyl ester

C₂₀H₃₂NO₆PSi

(S)-2-[(3-benzyloxycarbonylamino-3-methoxycarbonyl-propyl)-methoxy-phosphinoylmethyl]-pentanedioic acid

Refernces

• 1、 Barton, Derek H. R.,Crich, David,Herve, Yolande,Potier, Pierre,Thierry, Josiane. "THE FREE RADICAL CHEMISTRY OF CARBOXYLIC ESTERS OF 2-SELENOPYRIDINE-N-OXIDE: A CONVENIENT SYNTHESIS OF (L)-VINYLGLYCINE". . p. 4347 - 4358. Retrieved 2007/10/02.