L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester

Base Information

• Chemical Name: L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester
• CAS No.: 81135-30-0
• Molecular Formula: C₃₆H₆₀N₆O₇
• Molecular Weight: 688.908
• Mol file: 81135-30-0.mol

Synonyms:L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester

Chemical Property of L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester

There total 27 articles about L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl 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: 91.0%

N-(tert-butoxycarbonyl)-L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester (81135-29-7) → L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester (81135-30-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1021/jm00156a014

Reference yield:

N-(tert-Butyloxycarbonyl)-α-aminobutyrylsarcosine benzyl ester (81135-22-0) → L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester (81135-30-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 96.9 percent / H₂ / 10 percent Pd/C / ethanol / 2 h / Ambient temperature

2: 1.) pivaloyl chloride, N-methylmorpholine / 1.) CHCl₃, 1 h, r.t.; 2.) CHCl₃, 15 h, r.t.

3: 81.5 percent / CF₃COOH, NaHCO₃ / 15 h / -20 °C

With 4-methyl-morpholine; hydrogen; pivaloyl chloride; sodium hydrogencarbonate; trifluoroacetic acid; palladium on activated charcoal; In ethanol;

DOI:10.1002/hlca.19840670220

Reference yield:

H-Ala-OBzl (17831-01-5) → L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester (81135-30-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) pivaloyl chloride, N-methylmorpholine / 1.) CHCl₃, -20 deg C, 3 h; 2.) CHCl₃, -20 deg C, 15 h

2: 87 percent / CF₃COOH, NaHCO₃ / -20 °C

3: 1.) pivaloyl chloride, N-methylmorpholine / 1.) CHCl₃, 3 h -20 deg C; 2.) CHCl₃,18 h, -20 deg C

4: 96.7 percent / CF₃COOH, NaHCO₃ / 4 h / -20 °C

5: pivaloyl chloride, N-methylmorpholine / 1.) CHCl₃, 4 h, -20 deg C; 2.) CHCl₃, 15 h, -20 deg C

6: 98 percent / CF₃COOH, NaHCO₃ / trifluoroacetic acid / 16 h / -20 °C

7: 1.) pivaloyl chloride, N-methylmorpholine / 1.) CHCl₃, 1 h, r.t.; 2.) CHCl₃, 15 h, r.t.

8: 81.5 percent / CF₃COOH, NaHCO₃ / 15 h / -20 °C

With 4-methyl-morpholine; pivaloyl chloride; sodium hydrogencarbonate; trifluoroacetic acid; In trifluoroacetic acid;

DOI:10.1002/hlca.19840670220

upstream raw materials:

N-(tert-butoxycarbonyl)-L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester

t-Boc-L-valine

H-Ala-OBzl

N-t-butoxycarbonyl-N-methyl-L-leucine

Downstream raw materials:

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester

<<(4S,5R,3'E)-5-(1',1'-dimethyl-3'-pentenyl)-2,2,3-trimethyl-4-oxazolidinyl>carbonyl>-L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester

N-MeLeu(3-OH)-Abu-Sar-MeLeu-Val-MeLeu-Ala-OBzl

MeAbu-Abu-Sar-MeLeu-Val-MeLeu-Ala-OBzl

Refernces

• 1、 Rich, Daniel H.,Dhaon, Madhup K.,Dunlap, Brian,Miller, Stephen P. F.. "Synthesis and Antimitogenic Activities of Four Analogues of Cyclosporin A Modified in the 1-Position". . p. 978 - 984. Retrieved 2007/10/02.