Leucinostatin A

Base Information

• Chemical Name: Leucinostatin A
• CAS No.: 82111-44-2
• Molecular Formula: C₆₂H₁₁₁N₁₁O₁₃
• Molecular Weight: 1218.63
• Mol file: 82111-44-2.mol

Synonyms:Leucinostatin A;78149-02-7 (Hydrochloride);Antibiotic 1907-viii;Antibiotic cc 1014;Antibiotic p-168;beta-Alaninamide, cis-4-methyl-1-(4-methyl-1-oxo-2-hexenyl)-L-prolyl-(4S,6S)-6-hydroxy-4-methyl-8-oxo-L-2-aminodecanoyl-threo-3-hydroxy-L-leucyl-2-methylalanyl-L-leucyl-L-leucyl-2-methylalanyl-2-methylalanyl-N-(2-(dimethylamino)-1-methylethyl)-, (1(S-(E)),9(S))-;Nsc 356885

Chemical Property of Leucinostatin A

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1408°C at 760 mmHg
• Flash Point: 805.3°C
• Density: 1.116g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Leucinostatin A

There total 58 articles about Leucinostatin A 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: 32.0%

C61H120N10O11Si2 + (2S,4S)-4-methyl-1-((S,E)-4-methylhex-2-enoyl)pyrrolidine-2-carboxylic acid → leucinostatin A (82111-44-2)

Guidance literature:

(2S,4S)-4-methyl-1-((S,E)-4-methylhex-2-enoyl)pyrrolidine-2-carboxylic acid; With 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 N,N-dimethyl-formamide; at 0 ℃; for 0.5h; Molecular sieve;

C₆₁H₁₂₀N₁₀O₁₁Si₂; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h; Molecular sieve;

DOI:10.1002/chem.201703239

Reference yield:

C61H120N10O11Si2 + (2S,4S)-4-methyl-1-((S,E)-4-methylhex-2-enoyl)pyrrolidine-2-carboxylic acid → leucinostatin A (82111-44-2)

Guidance literature:

(2S,4S)-4-methyl-1-((S,E)-4-methylhex-2-enoyl)pyrrolidine-2-carboxylic acid; With 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 N,N-dimethyl-formamide; at 0 - 20 ℃; for 0.5h;

C₆₁H₁₂₀N₁₀O₁₁Si₂; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h;

DOI:10.1002/chem.201703239

Reference yield:

methyl (2S,4S)-2-(bis-(tert-butoxycarbonyl)amino)-4-methyl-6-oxohexanoate (1408286-93-0) → leucinostatin A (82111-44-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 2,2,5,7,8-pentamethylchroman-6-ol; mesitylcopper(I); (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane / N,N-dimethyl-formamide / 0.17 h / -60 °C

1.2: 48 h / -60 °C

2.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 - 20 °C

3.1: methyl trifluoromethanesulfonate / dichloromethane / 2.5 h / 40 °C

3.2: 3 h / -78 °C

4.1: trimethyltin(IV) hydroxide / dichloromethane / 120 °C / Sealed tube

5.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C

5.2: 4 h / 0 - 20 °C

6.1: boron trifluoride diethyl etherate / dichloromethane / 3 h / 0 - 20 °C / Molecular sieve

7.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C

7.2: 3 h / 0 - 20 °C

With 2,6-dimethylpyridine; 2,2,5,7,8-pentamethylchroman-6-ol; boron trifluoride diethyl etherate; mesitylcopper(I); N-ethyl-N,N-diisopropylamine; trimethyltin(IV) hydroxide; methyl trifluoromethanesulfonate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.201703239

upstream raw materials:

methyl (2S,4S)-2-(bis-(tert-butoxycarbonyl)amino)-4-methyl-6-oxohexanoate

Refernces