154161-01-0

Upstream product

• 154161-05-4 L-N-(benzyloxycarbonyl)-O-<(1,1-dimethylethyl)dimethylsilyloxy>serine methyl ester 
• 501-53-1 benzyl chloroformate 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 154659-09-3 (R)-benzyl (1-((tert-butyldimethylsilyl)oxy)-3-hydroxypropan-2-yl)carbamate 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 154659-20-8 (2S,3R,4R)-2--1-(tert-butyldimethylsilyloxy)octadecane-3,4-diol 
• 300699-05-2 (3S,4S)-4-Benzyloxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-pentanoic acid phenyl ester 
• 359455-05-3 [(1S,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-2-hydroxy-propyl]-carbamic acid benzyl ester 
• 154161-00-9 (1S,2S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-hydroxypent-4-enyl]carbamic acid benzyl ester 
• 823235-76-3 (3S,5S,6S)-6-benzyloxycarbonylamino-3,5,7-tris-(tert-butyl-dimethyl-silanyloxy)-heptanoic acid methyl ester 
• 823235-88-7 methyl (3S,5S,6S)-6-(((benzyloxy)carbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)-3,5-dihydroxyheptanoate 
• 823235-74-1 (5S,6S)-6-benzyloxycarbonylamino-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-3-oxo-heptanoic acid methyl ester 
• 154161-04-3 (2R,3S)-2-Formyl-3-triisopropylsilanyloxy-pyrrolidine-1-carboxylic acid benzyl ester 
• 179094-14-5 (1S,2S,3R,4R,5S,6R)-2,5-bis[N-(benzyloxycarbonyl)amino]-3,4-cyclohexylidene-1,3,4,6-cyclohexanetetrol 

Relevant academic research and scientific papers

C-Functionalized chiral dioxocyclam and cyclam derivatives with 1,2,3-triazole units: Synthesis, complexation properties and crystal structures of copper(ii) complexes

New C-functionalized syn- and anti-dioxocyclam and cyclam derivatives with 1,2,3-triazole units attached to carbon atoms within the skeleton were designed as valuable bifunctional chelating agents for applications in nuclear medicine. These macrocyclic chelators were prepared via a multi-step sequence involving α- and β-amino acids, and their copper(ii) complexation properties were evaluated. A solution structure in which the triazoles are in axially coordinating positions was proposed for the [Cu(anti-27)]2+ complex. Promising results have been obtained regarding the complexation kinetics (1/2 = 3.21 d, 5 M HCl, 50°C).

Synthesis of chiral branched allylamines through dual photoredox/nickel catalysis

Allylamines are versatile building blocks in the synthesis of various naturally occurring products and pharmaceuticals. In contrast to terminal allylamines, the methods of synthesis of their branched congeners with internal, stereodefined double bonds are less explored. This work describes a new approach for the preparation of allylaminesviacross-coupling of alkyl bromides with simple 3-bromoallylamines by merging the photoredox approach and Ni catalysis. The reaction proceeds under mild conditions, under blue light irradiation, and in the presence of an organic dye, 4CzIPN, as a photocatalyst. The scope of suitable reaction partners is broad, including alkyl bromides bearing reactive functionalities (e.g., esters, nitriles, aldehydes, ketones, epoxides) andN-protected allylamines, as well asN-allylated secondary and tertiary amines and heterocycles. The employment of non-racemic starting materials allows for rapid and easy construction of complex multifunctional allylamine derivatives without the loss of enantiomeric purity.

Synthesis of syn-vicinal diamines via the stereoselective allylation of acyclic chiral α-amino aldimines

The stereoselective allylation of acyclic chiral α-amino aldimines affording vicinal diamines, mediated by various Lewis acids (TiCl4, SnCl4, MgBr2·OEt2, BF3·OEt2, ZnCl2), is des

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 short and efficient synthesis of N-Cbz-galantinic acid under promoter control on enantioselective acyclic stereoselection based on chiral oxazaborolidinone-promoted aldol reactions

An effective 'promoter control' on enantioselective acyclic stereoselection based on chiral oxazaborolidinone-promoted asymmetric aldol reactions has been found in the case of chiral N-protected α-amino aldehydes. An enantioselective synthesis of the title compound has been efficiently accomplished by using a sequence of the aldol reaction. (C) 2000 Elsevier Science Ltd.

Effective and mild method for preparation of optically active α-amino aldehydes via TEMPO oxidation

The TEMPO oxidation method is successfully applied to preparation of variously protected, optically active α-amino aldehydes without racemization and in very good yield.

Synthesis of 1,4-diaminocyclitols from L-serine methyl ester

L-Serine methyl ester hydrochloride was converted to (S)-2-[N-(benzyloxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)propana l (6). Homocoupling of 6 promoted by [V2Cl3(THF)6]2[Zn2Cl6] (1) gave C2-symmetric diol (7). After manipulation of protecting groups and Swern oxidation, 7 was converted to a 1,6-dialdehyde 10. Intramolecular pinacol coupling of 10 with 1 gave a selectively protected 1,4-diamino-2,3,5,6-tetrahydroxycyclohexane, which is the key skeleton of Fortimicin AM and AK.

Pinacol cross coupling of 2-[N-(alkoxycarbonyl)amino] aldehydes and aliphatic aldehydes by [V2Cl3(THF)6]2[Zn2Cl 6]. Synthesis of syn,syn-3-[N-(alkoxycarbonyl)amino] 1,2-diols

Slow addition of 2-[N-(alkoxycarbonyl)amino] aldehydes to mixtures of [V2Cl3(THF)6]2[Zn2Cl 6] and aliphatic aldehydes gave syn,syn-3-[N-(alkoxycarbonyl)amino] 1,2-diols in good yield and high enantiomeric purity (>99:1). The alkyl group of the N-alkoxycarbonyl was shown to influence the yield: Me > allyl > Bn > t-Bu. Only the syn,syn diastereomer was observed (>20:1), except with N-Cbz-alaninal (10:1:1), O-benzyl-N-Cbz-serinal (7:1), and N-Cbz-prolinal (5:1 to 12:1). A new serinai derivative, N-Cbz-O-TBS-serinal, was cross coupled with n-pentadecanal to give a derivative of xylo-D-C18-phytosphingosine.

Highly Stereoselective Synthesis of cis-(2R,3S)-3-Hydroxyproline

Allyltrimethylsilane (5) reacted with N-carbobenzoxy-O-tert-butyldimethylsilyl-L-serinal (4) to give with high diastereoselectivity syn-adduct 3 which was subsequently transformed into cis-(2R,3S)-3-hydroxyproline (1).