752251-14-2

Basic information

• Product Name: (3R,5R,6S)-7-benzyloxy-6-benzyloxycarbonylamino-3,5-bis(tert-butyl-dimethylsilanyloxy)-heptanoic acid methyl ester
• Synonyms: (3R,5R,6S)-7-benzyloxy-6-benzyloxycarbonylamino-3,5-bis(tert-butyl-dimethylsilanyloxy)-heptanoic acid methyl ester
• CAS NO: 752251-14-2
• Molecular Weight: 660.011
• Mol File: 752251-14-2.mol

Chemical Properties

• CAS DataBase Reference: (3R,5R,6S)-7-benzyloxy-6-benzyloxycarbonylamino-3,5-bis(tert-butyl-dimethylsilanyloxy)-heptanoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,5R,6S)-7-benzyloxy-6-benzyloxycarbonylamino-3,5-bis(tert-butyl-dimethylsilanyloxy)-heptanoic acid methyl ester(752251-14-2)
• EPA Substance Registry System: (3R,5R,6S)-7-benzyloxy-6-benzyloxycarbonylamino-3,5-bis(tert-butyl-dimethylsilanyloxy)-heptanoic acid methyl ester(752251-14-2)

Safety Data

• Hazardous Substances Data: 752251-14-2(Hazardous Substances Data)

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 752251-12-0 (5R,6S)-7-benzyloxy-6-benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-oxoheptanoic acid methyl ester 
• 752251-11-9 (3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)pentanoic acid 
• 752251-10-8 (3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)pentanoic acid methyl ester 
• 752251-13-1 7-benzyloxy-(6S)-6-benzyloxycarbonylamino-(5R)-5-hydroxy-3-oxoheptanoic acid methyl ester 
• 752251-09-5 (3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-hydroxy-pentanoic acid methyl ester 
• 752251-08-4 (4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-oxo-pentanoic acid methyl ester 
• 20806-43-3 Z-Ser(Bzl)-OH 

Downstream Products

• 752251-16-4 (3R,5R,6S)-6-(2-benzyloxybenzoylamino)-3,5,7-tris-(tert-butyldimethylsilanyloxy)heptanoic acid 
• 752251-15-3 (3R,5R,6S)-6-(2-benzyloxy-benzoylamino)-3,5,7-tris-(tert-butyl-dimethyl-silanyloxy)heptanoic acid methyl ester 

Relevant articles and documents

Biomimetic total synthesis and antimicrobial evaluation of anachelin H

(Chemical Equation Presented) The first biomimetic total synthesis of the iron chelator anachelin H isolated from the cyanobacterium Anabaena cylindrica is reported. A first generation approach delivered one enantiomeric series of the polyketide fragment. Comparison of the 1H NMR data suggested the relative configuration of this anachelin fragment. The relative and absolute configuration of anachelin H was then established by total synthesis. A second generation approach involved the enzymatic conversion of N,N-dimethyltyramine to the anachelin chromophore. It was demonstrated that the enzyme tyrosinase is activated by the product during this reaction, the anachelin chromophore can serve as a tyrosinase activator. Anachelin H was evaluated against a panel of eleven bacterial and fungal pathogens, and moderate antibiotic activity (32 μg/mL) against Moraxella catarrhalis was found.

A biomimetic route to the peptide alkaloid anachelin

A postulated biogenesis forms the basis for a synthetic route to the natural product anachelin H (1). Key steps include a tellurium-mediated, oxidative aza annulation and a Claisen condensation under mild conditions. Experiments with a model substrate ind