Cyclo-

Base Information

• Chemical Name: Cyclo-
• CAS No.: 225780-88-1
• Molecular Formula: C₅₁H₇₅N₇O₁₂
• Molecular Weight: 978.196
• Mol file: 225780-88-1.mol

Synonyms:Cyclo-

Chemical Property of Cyclo-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclo-

There total 9 articles about Cyclo- 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:

α-Methyl (2R)-N-(tert-butoxycarbonyl)glutamate ester (55227-00-4) → Cyclo- (225780-88-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) DCC, HOAt, 2.) Et₃N / 1.) CH₂Cl₂, DMF, 0 deg C, 2 h; room temperature, 9 h, 2.) DMF, 0 deg C, 2.5 h; room temperature, 2.5 h

2: HATU, collidine / CH₂Cl₂ / 1.) 0 deg C, 12 h, 2.) room temperature, 12 h

3: tetrahydrofuran; H₂O / 8.5 h

4: 1.) TFA, 2.) Na₂CO₃, di-tert-butyldicarbonate / 1.) 50 min, 2.) H₂O, dioxane, 0 deg C, 2 h; room temperature, 6.5 h

5: 1.) H₂, TFA, 2.) HATU, collidine / 1.) 10 percent Pd/C / 1.) MeOH, 1 atm, 13 h, 2.) 0 deg C, 2 h; room temperature, 16 h

6: 1.) HOAt, DCC, 2.) TFA, 3.) collidine / 1.) DMF, CH₂Cl₂, 0 deg C, 2 h; room temperature, 7 h, 2.) 1.5 h, 3.) DMF, 0 deg C, 2 h; room temperature, 12 h

7: 1.) pentafluorophenol, DCC, 2.) TFA, 3.) phosphate buffer / 1.) EtOAc, 0 deg C, 1.5 h; room temperature, 6.5 h, 2.) 20 min, 3.) pH 9.5, 30 min

With 2,3,5-trimethyl-pyridine; 1-hydroxy-7-aza-benzotriazole; phosphate buffer; di-tert-butyl dicarbonate; 2,3,4,5,6-pentafluorophenol; hydrogen; sodium carbonate; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0968-0896(98)00254-5

Reference yield:

(2R,3S)-2-[Benzyl-(9-phenyl-9H-fluoren-9-yl)-amino]-3-methyl-succinic acid 1-methyl ester (184353-93-3) → Cyclo- (225780-88-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / HATU, iPr₂NEt / dimethylformamide / 1.) 0 deg C, 3 h, 2.) room temperature, 12 h

2: 1.) H₂, TFA, 2.) HATU, collidine / 1.) 10 percent Pd/C / 1.) MeOH, 1 atm, 13 h, 2.) 0 deg C, 2 h; room temperature, 16 h

3: 1.) HOAt, DCC, 2.) TFA, 3.) collidine / 1.) DMF, CH₂Cl₂, 0 deg C, 2 h; room temperature, 7 h, 2.) 1.5 h, 3.) DMF, 0 deg C, 2 h; room temperature, 12 h

4: 1.) pentafluorophenol, DCC, 2.) TFA, 3.) phosphate buffer / 1.) EtOAc, 0 deg C, 1.5 h; room temperature, 6.5 h, 2.) 20 min, 3.) pH 9.5, 30 min

With 2,3,5-trimethyl-pyridine; 1-hydroxy-7-aza-benzotriazole; phosphate buffer; 2,3,4,5,6-pentafluorophenol; hydrogen; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(98)00254-5

Reference yield:

Boc-D-iso-Glu(OMe)-α-dimethylphosphonylsarcosine (225780-71-2) → Cyclo- (225780-88-1)

Guidance literature:

Multi-step reaction with 6 steps

1: HATU, collidine / CH₂Cl₂ / 1.) 0 deg C, 12 h, 2.) room temperature, 12 h

2: tetrahydrofuran; H₂O / 8.5 h

3: 1.) TFA, 2.) Na₂CO₃, di-tert-butyldicarbonate / 1.) 50 min, 2.) H₂O, dioxane, 0 deg C, 2 h; room temperature, 6.5 h

4: 1.) H₂, TFA, 2.) HATU, collidine / 1.) 10 percent Pd/C / 1.) MeOH, 1 atm, 13 h, 2.) 0 deg C, 2 h; room temperature, 16 h

5: 1.) HOAt, DCC, 2.) TFA, 3.) collidine / 1.) DMF, CH₂Cl₂, 0 deg C, 2 h; room temperature, 7 h, 2.) 1.5 h, 3.) DMF, 0 deg C, 2 h; room temperature, 12 h

6: 1.) pentafluorophenol, DCC, 2.) TFA, 3.) phosphate buffer / 1.) EtOAc, 0 deg C, 1.5 h; room temperature, 6.5 h, 2.) 20 min, 3.) pH 9.5, 30 min

With 2,3,5-trimethyl-pyridine; 1-hydroxy-7-aza-benzotriazole; phosphate buffer; di-tert-butyl dicarbonate; 2,3,4,5,6-pentafluorophenol; hydrogen; sodium carbonate; dicyclohexyl-carbodiimide; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0968-0896(98)00254-5

upstream raw materials:

Boc-Adda-D-iso-Glu(OMe)-MeΔAla-D-Ala-3-cyclohexyl-L-Ala-D-β-Me-iso-Asp(OMe)-L-Ala-OH

α-Methyl (2R)-N-(tert-butoxycarbonyl)glutamate ester

(2R,3S)-2-[Benzyl-(9-phenyl-9H-fluoren-9-yl)-amino]-3-methyl-succinic acid 1-methyl ester

Boc-D-iso-Glu(OMe)-α-dimethylphosphonylsarcosine