(7R,14S)-14-Demethyl-7-de(1-methylpropyl)-14-phenylmethyl-7-(1-methylethyl)ulicyclamide

Base Information

• Chemical Name: (7R,14S)-14-Demethyl-7-de(1-methylpropyl)-14-phenylmethyl-7-(1-methylethyl)ulicyclamide
• CAS No.: 120853-17-0
• Molecular Formula: C38H41 N7 O5 S2
• Molecular Weight: 739.906
• Mol file: 120853-17-0.mol

Synonyms:Ulicyclamide,7-de(1-methylpropyl)-7-(1-methylethyl)-36-phenyl-;3H,12H-4,1:11,8:18,15-Trinitrilo-1H-pyrrolo[2,1-c][1,11,18,4,7,14,21]oxadithiatetraazacyclotetracosine,ulicyclamide deriv.;3H,12H-4,1:11,8:18,15-Trinitrilo-1H-pyrrolo[2,1-c][1,11,18,4,7,14,21]oxadithiatetraazacyclotetracosine-5,12,19,22(4H)-tetrone,6,7,13,14,20,21,24,25,26,26a-decahydro-3-methyl-7-(1-methylethyl)-14,21-bis(phenylmethyl)-,[3R-(3R*,4S*,7S*,14R*,21S*,26aS*)]-; Lissoclinamide 5

Chemical Property of (7R,14S)-14-Demethyl-7-de(1-methylpropyl)-14-phenylmethyl-7-(1-methylethyl)ulicyclamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1033.8°Cat760mmHg
• Flash Point: 579°C
• PSA: 221.93000
• Density: 1.46g/cm³
• LogP: 4.32840

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (7R,14S)-14-Demethyl-7-de(1-methylpropyl)-14-phenylmethyl-7-(1-methylethyl)ulicyclamide

There total 10 articles about (7R,14S)-14-Demethyl-7-de(1-methylpropyl)-14-phenylmethyl-7-(1-methylethyl)ulicyclamide 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: 73.0%

C38H43N7O6S2 (161006-68-4) → lissoclinamide 5 (120853-17-0)

Guidance literature:

With thionyl chloride; In dichloromethane; at 0 ℃; for 48h;

DOI:10.1016/0040-4039(94)88300-9

Reference yield:

2-[(R)-1-((2S,3S)-2-{[(S)-1-((S)-2-{[2-((S)-1-Amino-2-phenyl-ethyl)-thiazole-4-carbonyl]-amino}-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-hydroxy-butyrylamino)-2-methyl-propyl]-thiazole-4-carboxylic acid → lissoclinamide 5 (120853-17-0)

Guidance literature:

Multi-step reaction with 2 steps

1: diphenyl phosphorazide, N-methylmorpholine

2: 73 percent / thionyl chloride / CH₂Cl₂ / 48 h / 0 °C

With 4-methyl-morpholine; thionyl chloride; diphenyl phosphoryl azide; In dichloromethane;

DOI:10.1016/0040-4039(94)88300-9

Reference yield:

2-<(S)-1-t-butyloxycarbonylamino-2-phenyl-ethyl>-4-carboxythiazole (132402-81-4) → lissoclinamide 5 (120853-17-0)

Guidance literature:

Multi-step reaction with 7 steps

1: Huenig's base; pentafluorophenyl diphenylphosphinate / CH₂Cl₂ / 3.5 h / 0 - 25 °C

2: NaOH; H₂O / tetrahydrofuran / 1.5 h / 0 - 20 °C

3: Huenig's base; HOBt; DCC / dimethylformamide / 24 h / 0 - 20 °C

4: NaOH; H₂O / tetrahydrofuran; methanol / 1.5 h

5: CH₂Cl₂ / 2 h / 25 °C

6: N-methylmorpholine; diphenylphosphorazide / dimethylformamide / 50 h / 0 - 20 °C

7: 71 percent / SOCl₂ / CH₂Cl₂ / 36.5 h / 0 - 5 °C

With 4-methyl-morpholine; sodium hydroxide; thionyl chloride; diphenyl phosphoryl azide; pentafluorophenyl diphenyl-phosphinate; water; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: Hydrolysis / 3: Acylation / 4: Hydrolysis / 5: Substitution / 6: Acylation / 7: Dehydration;

DOI:10.1039/a909360e

upstream raw materials:

C₃₈H₄₃N₇O₆S₂

2-<(S)-1-t-butyloxycarbonylamino-2-phenyl-ethyl>-4-carboxythiazole

2(S)--3-phenylpropanimino ethyl ether

2-<(S)-1-t-butyloxycarbonylamino-2-phenyl-ethyl>-4-methoxycarbonylthiazole

Refernces

• 1、 Boden, Christopher,Pattenden, Gerald. "Total Synthesis of Lissoclinamide 5, a Cytotoxic Cyclic Peptide from the Tunicate Lissoclinum patella". . p. 8271 - 8274. Retrieved 2007/10/02.