131326-33-5

Upstream product

• 103202-59-1 6-(tert-butyldimethylsilyl)oxyhexan-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 629-11-8 1,6-hexanediol 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 131326-34-6 2,6-Bis-[6-(tert-butyl-dimethyl-silanyloxy)-hexyloxy]-benzoic acid methyl ester 
• 307965-12-4 1,6-hexanediol monoacetate p-toluenesulfonyl ester 
• 130157-26-5 2-[6-(2-Benzyloxycarbonylamino-acetylsulfanyl)-hexyloxy]-6-[6-((S)-2-tert-butoxycarbonylamino-propionylsulfanyl)-hexyloxy]-benzoic acid tert-butyl ester 
• 130157-30-1 2-[6-(2-Benzyloxycarbonylamino-acetylsulfanyl)-hexyloxy]-6-[6-((S)-2-tert-butoxycarbonylamino-propionylsulfanyl)-hexyloxy]-benzoic acid methyl ester 
• 131326-45-9 2-[6-(2-Benzyloxycarbonylamino-acetylsulfanyl)-hexyloxy]-6-(6-mercapto-hexyloxy)-benzoic acid tert-butyl ester 
• 131326-47-1 2-[6-(2-Benzyloxycarbonylamino-acetylsulfanyl)-hexyloxy]-6-(6-mercapto-hexyloxy)-benzoic acid methyl ester 
• 131326-37-9 2,6-Bis-(6-acetylsulfanyl-hexyloxy)-benzoic acid tert-butyl ester 
• 131326-38-0 2,6-Bis-(6-acetylsulfanyl-hexyloxy)-benzoic acid methyl ester 
• 130157-18-5 2,6-Bis-(6-mercapto-hexyloxy)-benzoic acid tert-butyl ester 
• 131326-35-7 2,6-Bis-(6-hydroxy-hexyloxy)-benzoic acid tert-butyl ester 
• 130157-22-1 2,6-Bis-(6-mercapto-hexyloxy)-benzoic acid methyl ester 
• 131326-36-8 2,6-Bis-(6-hydroxy-hexyloxy)-benzoic acid methyl ester 
• 130157-34-5 2-{6-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-propionylsulfanyl]-hexyloxy}-6-(6-mercapto-hexyloxy)-benzoic acid 
• 131355-34-5 2,6-Bis-[6-(tert-butyl-dimethyl-silanyloxy)-hexyloxy]-benzoic acid tert-butyl ester 

Relevant academic research and scientific papers

Diastereoselective synthesis and bioactivity of long-chain anti-2-amino-3-alkanols

An improved four-step approach for the stereoselective synthesis of long-chain anti-2-amino-3-alkanols is described. Using this method, the syntheses of antiproliferative (antitumoral) compounds, spisulosine (ES-285, 2), clavaminols A and B (3 and 4), the deacetylated products of clavaminols H and N (7 and 8), as well as (2S,3R)-2-aminododecan-3-ol (9) and xestoaminol C (10), have been achieved in excellent diastereoselectivities. In vitro study showed that these compounds induced cell death and dose-dependently inhibited cell proliferation in human glioblastoma cell line SHG-44, indicating the anti-tumor property of this series of compounds.

PEPTIDE BOND FORMATION USING AN ENZYME MIMICKING APPROACH

A man-made enzyme-model based on a concerted proton transfer step (bifunctional catalysis) which mimics the corresponding step in non-ribosomal peptide synthesis was developed.Important features of the model are the following: (a) a bifunctional acid-base catalyst for the thiolester aminolysis rate acceleration, (b) two thiol-containing arms mimicking the "swinging arms" of the enzyme, and (c) symmetry elements so that the process can be iterated with consequent formation of the polypeptide chain.Peptide bond formation was obtained by intramolecularly catalyzed thiolester aminolysis to give 5 in 80percent isolated yield (Scheme IV, V) and with at least a 103-fold rate acceleration in comparison with the corresponding non catalyzed process (4 -> 6)(Scheme IV, Table 1).The reaction is also 4-20 times faster than the analogous process 4 -> 6 run in the presence of 0.1M external catalyst (Et3N-ButCOOH or 2-Pyridone).Important structural and reaction parameters are discussed.A second intramolecular aminolysis reaction gave tripeptide 8 in lower yield (35percent) because of higher steric congestion in the transition state.