80963-10-6

Upstream product

• 186581-53-3 diazomethane 
• 23680-31-1 BOC-O-benzyl-L-serine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 19525-87-2 O-methyl O-benzyl-L-serinate hydrochloride 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 67-56-1 methanol 
• 78545-07-0 (S)-3-(benzoyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid 
• 65-85-0 benzoic acid 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 4726-96-9 O-Benzyl-L-serine 
• 74-88-4 methyl iodide 
• 27691-43-6 1-(benzylsulphanyl)-4-Nitrobenzene 

Downstream Products

• 79069-15-1 N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol 
• 500776-46-5 (S)-(1-benzyloxymethyl-2-hydroxy-2-methyl-propyl)carbamic acid tert-butyl ester 
• 936710-32-6 C₁₄H₁₇O₄N 
• 500776-47-6 (S)-4-benzyloxymethyl-5,5-dimethyloxazolidin-2-one 
• 500776-48-7 (S)-4-benzyloxymethyl-5,5-dimethyl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester 
• 228864-26-4 (E)-(R)-5-Benzyloxy-4-tert-butoxycarbonylamino-pent-2-enoic acid methyl ester 
• 213126-04-6 (E)-(R)-5-Benzyloxy-4-[3-(2-iodo-phenyl)-ureido]-pent-2-enoic acid methyl ester 
• 58577-87-0 O-benzyl-L-serinol 
• 158612-99-8 (4S)-4-[(benzyloxy)methyl]-1,3-oxazolidin-2-one 
• 159309-75-8 (S)-4-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyl)-oxazolidin-2-one 
• 143565-37-1 methyl 3-(benzyloxy)-2(S)-(1,3-dibenzylhexahydro-2-oxo-1,3,5-triazin-5-yl)-propionate 
• 126301-34-6 (S)-2-amino-3-benzyloxypropanesulphonic acid 
• 127407-54-9 (S)-2-t-butoxycarbonylamino-3-benzyloxy-1-methanesulfonyloxypropane 
• 126301-25-5 (S)-2-amino-3-benzyloxypropyl methanesulphonate hydrochloride 

Relevant academic research and scientific papers

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

Visible-Light Photocatalysis Employing Dye-Sensitized Semiconductor: Selective Aerobic Oxidation of Benzyl Ethers

The aerobic oxidation is an attractive approach toward environmentally benign synthesis of fine chemicals. In addition, dye-sensitized semiconductors are underdeveloped photocatalysts for selective organic synthesis. With the aid of catalytic eosin Y-sensitized titanium dioxide, we have developed efficient aerobic photooxidation of benzyl ethers to benzoates, featuring low cost, high atom economy, broad substrate scope, and user-friendly setup. Furthermore, preliminary mechanistic studies established that the reaction pathway likely entails a photoinduced, radical-based two-step process via an isolable peroxide intermediate.

Design, synthesis and anticancer mechanistic studies of linked azoles

Herein we report the synthesis and biological activity evaluation of 2,4 linked azole-containing molecules. A total of 13 linked thiazole- and oxazole-containing compounds were synthesized in good yields. Cytotoxicity evaluation of those compounds showed

Efficient Transfer of Chelating Amides into Different Types of Esters and Lactones

We describe a general and versatile approach for the conversion of carboxylic acid amides into their corresponding esters despite the fact that the former are thermodynamically more stable. The transformations are mediated by the coordination of CuI by a chelating entity. The resulting weakening of the amide bond allows for nucleophilic attack by alcoholic hydroxyl functions. The principle is demonstrated for a wide variety of transformations, leading to different kinds of esters and lactones. Due to their high resonance energy, amides are generally very stable towards solvolysis. However, bispicolylamides can be activated for alcoholysis by an unusual metal coordination involving the electron pair of the amide nitrogen. Herein, we widened the scope of the reaction by transforming the amides into a range of esters and lactones.

Synthesis of macrocycles that inhibit protein synthesis: Stereochemistry and structural based studies on sanguinamide B derivatives

We report the synthesis of seven new sanguinamide B (SanB) analogues. Substitution of amino acids along the backbone of SanB and testing in HCT-116 colon cancer cell lines identified new biologically active SanB derivatives. These compounds establish a st

Mechanistic studies of sanguinamide B derivatives: A unique inhibitor of eukaryotic ribosomes

Described are mechanistic studies of two Sanguinamide B (San B) derivatives. These compounds were identified as eukaryotic ribosomal inhibitors. Two biotinylated San B derivatives were synthesized and used to capture protein targets in a pull-down assay.

Novel branched isocyanides as useful building blocks in the Passerini-amine deprotection-acyl migration (PADAM) synthesis of potential HIV-1 protease inhibitors

Novel branched isocyanides have been prepared from l-serine and used as building blocks in the Passerini-amine deprotection-acyl migration (PADAM) sequence for the preparation of compounds with activity against HIV-1 protease.

The P1 N-isopropyl motif bearing hydroxyethylene dipeptide isostere analogues of aliskiren are in vitro potent inhibitors of the human aspartyl protease renin

Novel nonpeptide small molecule renin inhibitors bearing an N-isopropyl P1 motif were designed based on initial lead structures 1 and aliskiren (2). (P3-P1)-Benzamide derivatives such as 9a and 34, as well as the corresponding P1 basic tertiary amine derivatives 10 and 35 were found to display low nanomolar inhibition against human renin in vitro.

Efficient and convenient heterogeneous palladium-catalyzed regioselective deuteration at the benzylic position

The Pd/C-catalyzed efficient and regioselective hydrogen-deuterium (H-D) exchange reaction on the benzylic site proceeded in D2O in the presence of a small amount of H2 gas. The use of the Pd/C-ethylenediamine complex [Pd/C(en)] as a catalyst instead of Pd/C led to the efficient deuterium incorporation into the benzylic site of Obenzyl protective groups without hydrogenolysis. These H-D exchange reactions provide a post synthetic and D2-gas-free deuterium-labeling method on a wide variety of benzylic sites using D2O as the deuterium source and heterogeneous Pd/C or Pd/C(en) as a reusable heterogeneous palladium catalyst under mild and neutral conditions.

Pd-C-induced catalytic transfer hydrogenation with triethylsilane

(Chemical Equation Presented) In situ generation of molecular hydrogen by addition of triethylsilane to palladium-charcoal catalyst results in rapid and efficient reduction of multiple bonds, azides, imines, and nitro groups, as well as benzyl group and allyl group deprotection under mild, neutral conditions.