2-tert-butoxycarbonylamino-3-phenyl-thiopropionic acid S-(2-{[2-(6-amino-purin-9-yl)-ethoxymethyl]-[2-(2-tert-butoxycarbonylamino-3-phenyl-propionylsulfanyl)-ethoxy]-phosphinoyloxy}-ethyl) ester

Base Information

• Chemical Name: 2-tert-butoxycarbonylamino-3-phenyl-thiopropionic acid S-(2-{[2-(6-amino-purin-9-yl)-ethoxymethyl]-[2-(2-tert-butoxycarbonylamino-3-phenyl-propionylsulfanyl)-ethoxy]-phosphinoyloxy}-ethyl) ester
• CAS No.: 928651-91-6
• Molecular Formula: C₄₀H₅₄N₇O₁₀PS₂
• Molecular Weight: 888.015
• Mol file: 928651-91-6.mol

Synonyms:

Chemical Property of 2-tert-butoxycarbonylamino-3-phenyl-thiopropionic acid S-(2-{[2-(6-amino-purin-9-yl)-ethoxymethyl]-[2-(2-tert-butoxycarbonylamino-3-phenyl-propionylsulfanyl)-ethoxy]-phosphinoyloxy}-ethyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-tert-butoxycarbonylamino-3-phenyl-thiopropionic acid S-(2-{[2-(6-amino-purin-9-yl)-ethoxymethyl]-[2-(2-tert-butoxycarbonylamino-3-phenyl-propionylsulfanyl)-ethoxy]-phosphinoyloxy}-ethyl) ester

There total 3 articles about 2-tert-butoxycarbonylamino-3-phenyl-thiopropionic acid S-(2-{[2-(6-amino-purin-9-yl)-ethoxymethyl]-[2-(2-tert-butoxycarbonylamino-3-phenyl-propionylsulfanyl)-ethoxy]-phosphinoyloxy}-ethyl) 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:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → 2-tert-butoxycarbonylamino-3-phenyl-thiopropionic acid S-(2-{[2-(6-amino-purin-9-yl)-ethoxymethyl]-[2-(2-tert-butoxycarbonylamino-3-phenyl-propionylsulfanyl)-ethoxy]-phosphinoyloxy}-ethyl) ester (928651-91-6)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂S; isobutyl chloroformate; NMM / aq. HCl / tetrahydrofuran / -20 - -10 °C

2: NaH / tetrahydrofuran / -20 - 20 °C

3: N,N'-dicyclohexyl-4-morpholine carboxamidine / dimethylformamide / 20 - 80 °C

With 4-methyl-morpholine; N,N'-dicyclohexyl-4-morpholine carboxamidine; hydrogen sulfide; sodium hydride; isobutyl chloroformate; hydrogenchloride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.10.021

Reference yield:

2-tert-butoxycarbonylamino-3-phenyl-thiopropionic acid S-(2-bromo-ethyl) ester (928652-07-7) + Adefovir (106941-25-7) → 2-tert-butoxycarbonylamino-3-phenyl-thiopropionic acid S-(2-{[2-(6-amino-purin-9-yl)-ethoxymethyl]-[2-(2-tert-butoxycarbonylamino-3-phenyl-propionylsulfanyl)-ethoxy]-phosphinoyloxy}-ethyl) ester (928651-91-6)

Guidance literature:

With N,N'-dicyclohexyl-4-morpholine carboxamidine; In N,N-dimethyl-formamide; at 20 - 80 ℃;

DOI:10.1016/j.bmcl.2006.10.021

Reference yield:

(S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanethioic S-acid (81000-39-7) → 2-tert-butoxycarbonylamino-3-phenyl-thiopropionic acid S-(2-{[2-(6-amino-purin-9-yl)-ethoxymethyl]-[2-(2-tert-butoxycarbonylamino-3-phenyl-propionylsulfanyl)-ethoxy]-phosphinoyloxy}-ethyl) ester (928651-91-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / tetrahydrofuran / -20 - 20 °C

2: N,N'-dicyclohexyl-4-morpholine carboxamidine / dimethylformamide / 20 - 80 °C

With N,N'-dicyclohexyl-4-morpholine carboxamidine; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.10.021

upstream raw materials:

2-tert-butoxycarbonylamino-3-phenyl-thiopropionic acid S-(2-bromo-ethyl) ester

Adefovir

N-tert-butoxycarbonyl-L-phenylalanine

(S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanethioic S-acid