cyclo

Base Information

• Chemical Name: cyclo
• CAS No.: 225781-04-4
• Molecular Formula: C₅₂H₇₉N₇O₁₂
• Molecular Weight: 994.239
• Mol file: 225781-04-4.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 14 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:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → cyclo (225781-04-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) NaBH₃CN, 2.) conc. HCl / 1.) MeOH, 12 h, 2.) 3 h

2: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 1.) reflux, 10 h, 2.) room temperature, overnight

3: 88 percent / 1.0 LiOH / tetrahydrofuran / 26 h

4: 91 percent / HOBt, EDCI / CH₂Cl₂; dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temperature, 11 h

5: H₂ / Pd/C / methanol / 4.2 h / 760 Torr

6: 75 percent / HATU, collidine / dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temperature, 10 h

7: 1.) TFA, 2.) Na₂CO₃, di-tert-butyldicarbonate / 1.) 1.5 h, 2.) H₂O, dioxane, 0 deg C, 2 h; room temperature, 6.5 h

8: 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

9: 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

10: 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; hydrogenchloride; dmap; lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; phosphate buffer; di-tert-butyl dicarbonate; 2,3,4,5,6-pentafluorophenol; hydrogen; sodium cyanoborohydride; sodium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 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; methanol; dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

N-(cyclohexyl)-glycine ethyl ester hydrochloride → cyclo (225781-04-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 1.) reflux, 10 h, 2.) room temperature, overnight

2: 88 percent / 1.0 LiOH / tetrahydrofuran / 26 h

3: 91 percent / HOBt, EDCI / CH₂Cl₂; dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temperature, 11 h

4: H₂ / Pd/C / methanol / 4.2 h / 760 Torr

5: 75 percent / HATU, collidine / dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temperature, 10 h

6: 1.) TFA, 2.) Na₂CO₃, di-tert-butyldicarbonate / 1.) 1.5 h, 2.) H₂O, dioxane, 0 deg C, 2 h; room temperature, 6.5 h

7: 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

8: 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

9: 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; dmap; lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; phosphate buffer; di-tert-butyl dicarbonate; 2,3,4,5,6-pentafluorophenol; hydrogen; sodium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 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; methanol; dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

D-Ala-L-Leu-O-tBu (78031-82-0) → cyclo (225781-04-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 91 percent / HOBt, EDCI / CH₂Cl₂; dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temperature, 11 h

2: H₂ / Pd/C / methanol / 4.2 h / 760 Torr

3: 75 percent / HATU, collidine / dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temperature, 10 h

4: 1.) TFA, 2.) Na₂CO₃, di-tert-butyldicarbonate / 1.) 1.5 h, 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; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 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 methanol; dichloromethane; N,N-dimethyl-formamide;

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

upstream raw materials:

Boc-Adda-D-iso-Glu(OMe)-N-(cyclohexyl)-Gly-D-Ala-L-Leu-D-β-Me-iso-Asp(OMe)-L-Ala-OH

N-Cbz-(D)-Ala-(L)-Leu-O-tBu

cyclohexanone

D-Ala-L-Leu-O-tBu