Topostin D-654

Base Information

• Chemical Name: Topostin D-654
• CAS No.: 179095-19-3
• Molecular Formula: C37H70N2O7
• Molecular Weight: 654.96
• Mol file: 179095-19-3.mol

Synonyms:13-Methyl-tetradecanoic acid (R)-1-({[((S)-1-carboxy-2-hydroxy-ethylcarbamoyl)-methyl]-carbamoyl}-methyl)-13-methyl-tetradecyl ester;N-{N-[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]glycyl}-L-serine;

Chemical Property of Topostin D-654

Chemical Property:

• PSA: 142.03000
• LogP: 8.64220

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Topostin D-654

There total 27 articles about Topostin D-654 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: 74.0%

(R)-1-((2-(((S)-3-hydroxy-1-methoxy-1-oxopropan-2-yl)amino)-2-oxoethyl)amino)-15-methyl-1-oxohexadecan-3-yl 13-methyltetradecanoate (103196-65-2) → (3R)-N-<3-(13'-methyltetradecanoyloxy)-15-methylhexadecanoyl>glycyl-L-serine (179095-19-3,96095-04-4)

Guidance literature:

With potassium trimethylsilonate; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1016/j.tet.2016.10.010

Reference yield: 70.0%

N-{N-[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]glycyl}-L-serine benzyl ester (214406-45-8) → (3R)-N-<3-(13'-methyltetradecanoyloxy)-15-methylhexadecanoyl>glycyl-L-serine (179095-19-3,96095-04-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 2.5h; Ambient temperature;

DOI:10.1016/S0040-4020(98)83044-5

Reference yield:

13-methyltetradecanoic acid (2485-71-4) → (3R)-N-<3-(13'-methyltetradecanoyloxy)-15-methylhexadecanoyl>glycyl-L-serine (179095-19-3,96095-04-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / DCC, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

2: 90 percent / H₂ / Pd(OH)2/C / ethanol / 2 h / Ambient temperature

3: oxalyl chloride / CH₂Cl₂ / 1 h / Ambient temperature

4: Et₃N / CH₂Cl₂ / 1 h / 0 - 5 °C

5: 98 percent / H₂ / Pd/C / ethyl acetate / 2 h / Ambient temperature

6: 72 percent / DCC / CH₂Cl₂ / 2 h / Ambient temperature

7: 70 percent / H₂ / Pd/C / ethyl acetate / 2.5 h / Ambient temperature

With dmap; oxalyl dichloride; hydrogen; triethylamine; dicyclohexyl-carbodiimide; palladium dihydroxide; palladium on activated charcoal; In ethanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4020(98)83044-5

upstream raw materials:

L-serin

N-{N-[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]glycyl}-L-serine benzyl ester

13-methyltetradecanoic acid

(3R)-ethyl-3-hydroxy-15-methylhexadecanoate

Downstream raw materials:

13-methyltetradecanoic acid

(3R)-ethyl-3-hydroxy-15-methylhexadecanoate

Refernces

• 1、 Dietz, Christopher,Hart, Theresa K.,Nemati, Reza,Yao, Xudong,Nichols, Frank C.,Smith, Michael B.. "Structural verification via convergent total synthesis of dipeptide–lipids isolated from Porphyromonas gingivalis". . p. 7557 - 7569. Retrieved 2016/11/11.
• 2、 Shioiri, Takayuki,Terao, Yoshihiro,Irako, Naoko,Aoyama, Toyohiko. "Synthesis of topostins B567 and D654 (WB-3559D, flavolipin), DNA topoisomerase I inhibitors of bacterial origin". . p. 15701 - 15710. Retrieved 2007/10/03.