N-BOC-S-TRITYLCYSTEIN-N-METHOXY-N-METHYLAMIDE

Base Information

• Chemical Name: N-BOC-S-TRITYLCYSTEIN-N-METHOXY-N-METHYLAMIDE
• CAS No.: 158861-38-2
• Molecular Formula: C29H34N2O4S
• Molecular Weight: 506.666
• Mol file: 158861-38-2.mol

Synonyms:N-BOC-S-TRITYLCYSTEIN-N-METHOXY-N-METHYLAMIDE;[(1R)-2-(MethoxyMethylaMino)-2-oxo-1-[[(triphenylMethyl)thio]Methyl]ethyl]carbaMic Acid 1,1-DiMethylethyl Ester

Chemical Property of N-BOC-S-TRITYLCYSTEIN-N-METHOXY-N-METHYLAMIDE

Chemical Property:

• PSA: 96.66000
• Density: 1.164g/cm³
• LogP: 5.82920
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

N-Boc-S-tritylcystein-N-methoxy-N-methylamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-BOC-S-TRITYLCYSTEIN-N-METHOXY-N-METHYLAMIDE

There total 4 articles about N-BOC-S-TRITYLCYSTEIN-N-METHOXY-N-METHYLAMIDE 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: 97.0%

N-tert-butyloxycarbonyl-S-trityl-L-cysteine (21947-98-8,87494-13-1) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → (R)-N-methyl-N-methoxy-2-tert-butoxycarbonylamino-3-(triphenylmethylthio)propionamide (158861-38-2)

Guidance literature:

N-tert-butyloxycarbonyl-S-trityl-L-cysteine; With 4-methyl-morpholine; isobutyl chloroformate; In dichloromethane; at -15 ℃; for 0.25h;

N,O-dimethylhydroxylamine*hydrochloride; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/ol051489+

Reference yield: 92.0%

→ (R)-N-methyl-N-methoxy-2-tert-butoxycarbonylamino-3-(triphenylmethylthio)propionamide (158861-38-2)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

Reference yield:

N-tert-butyloxycarbonyl-S-trityl-L-cysteine (21947-98-8,87494-13-1) → (R)-N-methyl-N-methoxy-2-tert-butoxycarbonylamino-3-(triphenylmethylthio)propionamide (158861-38-2)

Guidance literature:

Multi-step reaction with 2 steps

1: N-methylpiperidine / CH₂Cl₂ / 0.08 h / -20 °C

2: N-methylpiperidine / CH₂Cl₂

With N-methylcyclohexylamine; In dichloromethane;

DOI:10.1021/jm00032a004

upstream raw materials:

N,O-dimethylhydroxylamine*hydrochloride

N-tert-butyloxycarbonyl-S-trityl-L-cysteine

Downstream raw materials:

pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3,6-dimethyl-5-(2,2,2-trichloroethoxycarbonyloxy)-hept-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester

C₂₉H₃₃NO₄S

ethyl (R)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-pentanonate

ethyl (R,E-)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-penta-2-enoate

Refernces

• 1、 Chen, Qi-Yin,Liu, Yanxia,Cai, Weijing,Luesch, Hendrik. "Improved total synthesis and biological evaluation of potent apratoxin S4 based anticancer agents with differential stability and further enhanced activity". supporting information. p. 3011 - 3029. Retrieved 2014/05/06.
• 2、 Qian, Yimin,Vogt, Andreas,Sebti, Sa?d M.,Hamilton, Andrew D.. "Design and synthesis of non-peptide Ras CAAX mimetics as potent farnesyltransferase inhibitors". . p. 217 - 223. Retrieved 2007/10/03.