cyclothialidine

Base Information

• Chemical Name: cyclothialidine
• CAS No.: 147214-63-9
• Molecular Formula: C26H35 N5 O12 S
• Molecular Weight: 641.656
• Mol file: 147214-63-9.mol

Synonyms:L-Alanine,N-[S-[(2-carboxy-4,6-dihydroxy-3-methylphenyl)methyl]-N-[N-(cis-3-hydroxy-1-L-seryl-L-prolyl)-L-seryl]-L-cysteinyl]-,k-lactone;9,2,5-Benzoxathiaazacyclododecine, cyclic peptide deriv.; Cyclothialidine; Ro09-1437

Chemical Property of cyclothialidine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1253.4°Cat760mmHg
• PKA: 3.61±0.10(Predicted)
• Flash Point: 711.8°C
• PSA: 303.45000
• Density: 1.6g/cm³
• LogP: -1.60110

Purity/Quality:

98% ^*data from raw suppliers

CYCLOTHIALIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of cyclothialidine

There total 23 articles about cyclothialidine 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: 43.0%

tert-butyl N-[(4R,7S)-7-({(3R)-1-[N-(tert-butoxycarbonyl)-L-seryl]-3-hydroxy-L-prolyl}amino)-1,3,4,5,6,7,8,10-octahydro-12,14-dihydroxy-11-methyl-6,10-dioxo-9,2,5-benzoxathiazacyclododecin-4-ylcarbonyl]-L-alaninate (186132-93-4) → cyclothialidine (147214-63-9)

Guidance literature:

With trifluoroacetic acid; at 0 ℃; for 1.75h;

DOI:10.1002/hlca.19960790816

Reference yield:

3,5-Dihydroxybenzoic acid (99-10-5) → cyclothialidine (147214-63-9)

Guidance literature:

Multi-step reaction with 17 steps

1: 92 percent / H₂O; ethanol / 15 h / Ambient temperature; pH 5

2: 88 percent / H₂, piperidine / 5percent Pd/C / methanol; H₂O / 14 h / 75.01 Torr

3: 58 percent / H₂O; ethanol / 15 h / Ambient temperature; pH 5

4: 70 percent / H₂, 3N NaOH / 5percent Pd/C / methanol; H₂O / 14 h / 75.01 Torr

5: 82 percent / N,N,N',N'-tetramethylguanidine / dimethylformamide / 6 h / Ambient temperature

6: 91 percent / Et₃N / dimethylformamide / 1.5 h / 0 °C

7: 67 percent / N-bromosuccinimide / CCl₄ / 0.83 h / Heating; Irradiation

8: 54 percent / Et₃N / CH₂Cl₂ / 0 deg C, 1 h; room temp., 2 h

9: 93 percent / H₂ / 5percent Pd/C / ethyl acetate / 15 h / Ambient temperature

10: 86 percent / Ph₃P, 95percent diethyl azodicarboxylate / toluene / 0 deg C, 15 min; room temp., 4 h

11: 76 percent / CF₃COOH / 0.5 h / 0 °C

12: 90 percent / N-<3-(dimethylamino)propyl>-N'-ethylcarbodiimide hydrochloride / acetonitrile / 5 h / 0 °C

13: 89 percent / CF₃COOH / 0.5 h / 0 °C

14: 73 percent / N-<3-(dimethylamino)propyl>-N'-ethylcarbodiimide hydrochloride / acetonitrile / 5 h / 0 °C

15: 1.) NH₄F, 2.) 1N NaOH / 1.) 80percent aq. THF, room temp., 40 min, 2.) water, THF

16: 75 percent / N-hydroxysuccinimide, N-<3-(dimethylamino)propyl>-N'-ethylcarbodiimide hydrochloride; N-methylmorpholine / acetonitrile / 0 deg C, 3 h; room temp., 2 h

17: 43 percent / CF₃COOH / 1.75 h / 0 °C

With piperidine; 4-methyl-morpholine; ammonium fluoride; sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; N-Bromosuccinimide; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; N,N,N',N'-tetramethylguanidine; palladium on activated charcoal; In methanol; tetrachloromethane; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/hlca.19960790816

Reference yield:

3,5-dihydroxy-2-methylbenzoic acid (4780-63-6) → cyclothialidine (147214-63-9)

Guidance literature:

Multi-step reaction with 15 steps

1: 58 percent / H₂O; ethanol / 15 h / Ambient temperature; pH 5

2: 70 percent / H₂, 3N NaOH / 5percent Pd/C / methanol; H₂O / 14 h / 75.01 Torr

3: 82 percent / N,N,N',N'-tetramethylguanidine / dimethylformamide / 6 h / Ambient temperature

4: 91 percent / Et₃N / dimethylformamide / 1.5 h / 0 °C

5: 67 percent / N-bromosuccinimide / CCl₄ / 0.83 h / Heating; Irradiation

6: 54 percent / Et₃N / CH₂Cl₂ / 0 deg C, 1 h; room temp., 2 h

7: 93 percent / H₂ / 5percent Pd/C / ethyl acetate / 15 h / Ambient temperature

8: 86 percent / Ph₃P, 95percent diethyl azodicarboxylate / toluene / 0 deg C, 15 min; room temp., 4 h

9: 76 percent / CF₃COOH / 0.5 h / 0 °C

10: 90 percent / N-<3-(dimethylamino)propyl>-N'-ethylcarbodiimide hydrochloride / acetonitrile / 5 h / 0 °C

11: 89 percent / CF₃COOH / 0.5 h / 0 °C

12: 73 percent / N-<3-(dimethylamino)propyl>-N'-ethylcarbodiimide hydrochloride / acetonitrile / 5 h / 0 °C

13: 1.) NH₄F, 2.) 1N NaOH / 1.) 80percent aq. THF, room temp., 40 min, 2.) water, THF

14: 75 percent / N-hydroxysuccinimide, N-<3-(dimethylamino)propyl>-N'-ethylcarbodiimide hydrochloride; N-methylmorpholine / acetonitrile / 0 deg C, 3 h; room temp., 2 h

15: 43 percent / CF₃COOH / 1.75 h / 0 °C

With 4-methyl-morpholine; ammonium fluoride; sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; N-Bromosuccinimide; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; N,N,N',N'-tetramethylguanidine; palladium on activated charcoal; In methanol; tetrachloromethane; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/hlca.19960790816

upstream raw materials:

tert-butyl N-[(4R,7S)-7-({(3R)-1-[N-(tert-butoxycarbonyl)-L-seryl]-3-hydroxy-L-prolyl}amino)-1,3,4,5,6,7,8,10-octahydro-12,14-dihydroxy-11-methyl-6,10-dioxo-9,2,5-benzoxathiazacyclododecin-4-ylcarbonyl]-L-alaninate

3,5-Dihydroxybenzoic acid

3,5-dihydroxy-2-methylbenzoic acid

cis-N-(tert-butoxycarbonyl)-3-hydroxy-DL-proline

Downstream raw materials:

L-alanin

L-serin

L-Cysteine

(2S,3R)-3-hydroxyproline

Refernces