(S)-2-[(R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-(4-aminomethyl-5-hydroxy-6-methyl-pyridin-3-ylmethylsulfanyl)-propionylamino]-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-[(R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-(4-aminomethyl-5-hydroxy-6-methyl-pyridin-3-ylmethylsulfanyl)-propionylamino]-propionic acid methyl ester
• CAS No.: 849771-02-4
• Molecular Formula: C₂₆H₃₅N₅O₆S
• Molecular Weight: 545.66
• Mol file: 849771-02-4.mol

Synonyms:(S)-2-[(R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-(4-aminomethyl-5-hydroxy-6-methyl-pyridin-3-ylmethylsulfanyl)-propionylamino]-propionic acid methyl ester

Chemical Property of (S)-2-[(R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-(4-aminomethyl-5-hydroxy-6-methyl-pyridin-3-ylmethylsulfanyl)-propionylamino]-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-(4-aminomethyl-5-hydroxy-6-methyl-pyridin-3-ylmethylsulfanyl)-propionylamino]-propionic acid methyl ester

There total 11 articles about (S)-2-[(R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-(4-aminomethyl-5-hydroxy-6-methyl-pyridin-3-ylmethylsulfanyl)-propionylamino]-propionic 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: 95.0%

(S)-2-{(R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-[4-(tert-butoxycarbonylamino-methyl)-5-methoxymethoxy-6-methyl-pyridin-3-ylmethylsulfanyl]-propionylamino}-propionic acid methyl ester (849771-01-3) → (S)-2-[(R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-(4-aminomethyl-5-hydroxy-6-methyl-pyridin-3-ylmethylsulfanyl)-propionylamino]-propionic acid methyl ester (849771-02-4)

Guidance literature:

With trifluoroacetic acid;

DOI:10.1016/j.bmcl.2005.01.021

Reference yield:

(S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) → (S)-2-[(R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-(4-aminomethyl-5-hydroxy-6-methyl-pyridin-3-ylmethylsulfanyl)-propionylamino]-propionic acid methyl ester (849771-02-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / HATU; i-Pr₂NEt

2: 70 percent / LiOH / tetrahydrofuran

3: 82 percent / HATU; i-Pr₂NEt

4: 95 percent / TFA

With lithium hydroxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2005.01.021

Reference yield:

pyridoxamine (85-87-0) → (S)-2-[(R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-(4-aminomethyl-5-hydroxy-6-methyl-pyridin-3-ylmethylsulfanyl)-propionylamino]-propionic acid methyl ester (849771-02-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / Et₃N

2: 95 percent / imidazole

3: 75 percent / NaH

4: 86 percent / TBAF

5: 100 percent / Et₃N

6: 87 percent / NaH

7: 95 percent / HATU; i-Pr₂NEt

8: 70 percent / LiOH / tetrahydrofuran

9: 82 percent / HATU; i-Pr₂NEt

10: 95 percent / TFA

With 1H-imidazole; lithium hydroxide; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2005.01.021

upstream raw materials:

(S)-2-{(R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-[4-(tert-butoxycarbonylamino-methyl)-5-methoxymethoxy-6-methyl-pyridin-3-ylmethylsulfanyl]-propionylamino}-propionic acid methyl ester

(S)-2-acetylamino-3-phenylpropanoic acid

pyridoxamine

(3-hydroxy-5-hydroxymethyl-2-methylpyridin-4-ylmethyl)carbamic acid tert-butyl ester