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

Base Information

• Chemical Name: (R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-[4-(tert-butoxycarbonylamino-methyl)-5-methoxymethoxy-6-methyl-pyridin-3-ylmethylsulfanyl]-propionic acid
• CAS No.: 849771-00-2
• Molecular Formula: C₂₉H₄₀N₄O₈S
• Molecular Weight: 604.725
• Mol file: 849771-00-2.mol

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

Chemical Property of (R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-[4-(tert-butoxycarbonylamino-methyl)-5-methoxymethoxy-6-methyl-pyridin-3-ylmethylsulfanyl]-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-[4-(tert-butoxycarbonylamino-methyl)-5-methoxymethoxy-6-methyl-pyridin-3-ylmethylsulfanyl]-propionic acid

There total 10 articles about (R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-[4-(tert-butoxycarbonylamino-methyl)-5-methoxymethoxy-6-methyl-pyridin-3-ylmethylsulfanyl]-propionic acid 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: 70.0%

(R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-[4-(tert-butoxycarbonylamino-methyl)-5-methoxymethoxy-6-methyl-pyridin-3-ylmethylsulfanyl]-propionic acid ethyl ester → (R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-[4-(tert-butoxycarbonylamino-methyl)-5-methoxymethoxy-6-methyl-pyridin-3-ylmethylsulfanyl]-propionic acid (849771-00-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2005.01.021

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-[4-(tert-butoxycarbonylamino-methyl)-5-methoxymethoxy-6-methyl-pyridin-3-ylmethylsulfanyl]-propionic acid (849771-00-2)

Guidance literature:

Multi-step reaction with 8 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

With 1H-imidazole; lithium hydroxide; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; 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:

(S)-2-acetylamino-3-phenylpropanoic acid (2018-61-3) → (R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-[4-(tert-butoxycarbonylamino-methyl)-5-methoxymethoxy-6-methyl-pyridin-3-ylmethylsulfanyl]-propionic acid (849771-00-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / HATU; i-Pr₂NEt

2: 70 percent / LiOH / tetrahydrofuran

With lithium hydroxide; N-ethyl-N,N-diisopropylamine; 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:

di-tert-butyl dicarbonate

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

pyridoxamine

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

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