(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe

Base Information

• Chemical Name: (3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe
• CAS No.: 159173-45-2
• Molecular Formula: C₃₀H₄₆N₄O₄S
• Molecular Weight: 558.786
• Mol file: 159173-45-2.mol

Synonyms:(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe

Chemical Property of (3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe

There total 34 articles about (3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe 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: 99.0%

Boc-(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe (148597-90-4) → (3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe (159173-45-2)

Guidance literature:

With trifluoroacetic acid; for 0.5h;

DOI:10.1016/S0040-4020(01)80692-X

Reference yield:

N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7) → (3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe (159173-45-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: N,N'-carbonyldiimidazole; magnesium chloride; triethylamine / tetrahydrofuran / 3 h / 20 °C

1.2: 88 percent / triethylamine; anhydrous magnesium chloride / tetrahydrofuran / 39 h / 20 °C

2.1: 100 percent / hydrogen chloride / ethanol / 2 h / 0 °C

3.1: hydrogen / [RuBr₂((R)-2,2'-(Ph₂P)2-6,6'-(MeO)2-1,1'-biphenyl)] / ethanol / 24 h / 50 °C / 9120.61 Torr

4.1: 74 percent / LiHMDS; HMPA / tetrahydrofuran / 0.42 h / -20 °C

5.1: 81 percent / aq. NaOH / ethanol / 16 h / 20 °C

6.1: 72 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 16 h / 0 - 20 °C

7.1: trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; diethyl cyanophosphonate; hydrogen; triethylamine; 1,1'-carbonyldiimidazole; trifluoroacetic acid; magnesium chloride; lithium hexamethyldisilazane; [RuBr₂((R)-2,2'-(Ph₂P)2-6,6'-(MeO)2-1,1'-biphenyl)]; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2007.03.036

Reference yield:

tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidine-1-carboxylate (120205-54-1) → (3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe (159173-45-2)

Guidance literature:

Multi-step reaction with 3 steps

1: trifluoroacetic acid / CH₂Cl₂ / 1.5 h / 20 °C

2: 72 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 16 h / 0 - 20 °C

3: trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

With diethyl cyanophosphonate; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2007.03.036

upstream raw materials:

Cbz-Dil-Dap-Doe

Boc-(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe

ethyl (3R,4S,5S)-4-(N-tert-butoxycarbonyl-N-methylamino)-3-methoxy-5-methyl-heptanoate

N-(tert-butyloxycarbonyl)-L-isoleucine

Downstream raw materials:

dolastatin 10

Boc-(S)-Val-(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe

Refernces

• 1、 Roux, Florence,Maugras, Isabelle,Poncet, Joel,Niel, Gilles,Jouin, Patrick. "-". . p. 5345 - 5360. Retrieved 2007/10/02.
• 2、 Tomioka, Kiyoshi,Kanai, Motomu,Koga, Kenji. "An expeditious synthesis of dolastatin 10". . p. 2395 - 2398. Retrieved 2007/10/02.