324752-72-9

Upstream product

• 82353-56-8 (2R)-2-N-t-butoxycarbonyl-aminopropanal 
• 762-72-1 allyl-trimethyl-silane 
• 79069-50-4 Boc-Ala-H 
• 106-95-6 allyl bromide 
• 107-37-9 allyltrichlorosilane 
• 174851-37-7 (4R,5R)-5-allyl-4-methyl-2-oxazolidinone 
• 115269-78-8 (4R,5R)-5-allyl-4-methoxy-2-oxazolidinone 
• 174787-76-9 (4R,5R)-5-allyl-3-tert-butoxycarbonyl-4-methyl-2-oxazolidinone 
• 7393-43-3 tetraallyl tin 
• 24424-99-5 di-tert-butyl dicarbonate 
• 15761-38-3 L-N-Boc-Ala 
• 1294446-91-5 (S)-tert-butyl-N-(3-oxohex-5-en-2-yl)carbamate 
• 85116-38-7 (-)-B-allyldiisopinocampheylborane 
• 1730-25-2 allylmagnesium bromide 

Relevant academic research and scientific papers

A simple one pot procedure for the generation of homoallylic alcohols from acetals and amino acids

Treatment of acetals (1 and 2) and amino acetals (3-5) with either trifluoroacetic acid (TFA) or silica gel followed by tetraallyltin gave excellent yields of the corresponding homoallylic alcohols (68 - 100%).

Synthesis and characterization of some atypical sphingoid bases

Sphingolipids are ubiquitous and abundant components of all eukaryotic and some prokaryotic organisms. Sphingolipids show a large structural variety not only between the different species, but also within an individual cell. This variety is not limited to alterations in the polar headgroups of e.g. glycosphingolipids, but also affects the lipophilic anchors comprised of different fatty acids on the one hand and different sphingoid bases on the other hand. The structural variations within different sphingoid bases e.g. in pathogens can be used to identify novel biomarkers and drug targets and the specific change in the profile of common and uncommon sphingolipids are associated with pathological conditions like diabetes or cancer. Therefore, the emerging field of sphingolipidomics is dedicated to collect data on the sphingolipidome of a cell and hence to assign changes therein to certain states of a cell or to pathological conditions. This powerful tool however is still limited by the availability of structural information about the individual lipid species as well as by the availability of appropriate internal standards for quantification. Herein we describe the synthesis of a variety of 1-deoxy-sphingoid bases. 1-DeoxySphingolipids have recently acquired significant attention due to its pathological role in the rare inherited neuropathy, HSAN1 but also as predictive biomarkers in diabetes type II. Some of the compounds synthesized and characterized herein, have been used and will be used to elucidate the correct structure of these disease-related lipids and their metabolites.

PYRIMIDINE CARBOXAMIDES AS GSK-3 INHIBITORS

The disclosure generally relates to compounds of formula I, including their salts, as well as compositions and methods of using the compounds to treat disorders associated with GSK-3.

Exploring Leishmania major Inositol Phosphorylceramide Synthase (LmjIPCS): Insights into the ceramide binding domain

The synthesis of set of ceramide analogues exploring hydrophobicity in the acyl chains and the degree and nature of hydroxylation is described. These have been assayed against the parasitic protozoan enzyme LmjIPCS. These studies showed that whilst the C-3 hydroxyl group was not essential for turnover it provided enhanced affinity. Reflecting the membrane bound nature of the enzyme a long (C13) hydrocarbon ceramide tail was necessary for both high affinity and turnover. Whilst the N-acyl chain also contributed to affinity, analogues lacking the amide linkage functioned as competitive inhibitors in both enzyme and cell-based assays. A model that accounts for this observation is proposed.

A facile approach to trans-4,5-pyrrolidine lactam and application in the synthesis of nemonapride and streptopyrrolidine

An efficient approach to trans-4-hydroxylpyrrolidine lactams 1 starting from amino acid is described. The utility of this method has been demonstrated in the synthesis of antipsychotic nemonapride 3 and antiangiogenic streptopyrrolidine 4. Compared four s

A facile access to pyrroles from amino acids via an aza-Wacker cyclization

(Chemical Equation Presented) A facile and efficient synthesis of pyrroles from readily available amino acids is described. The key step in the method is an aza-Wacker oxidative cyclization catalyzed by palladium(II)/Cu(OTf) 2. A series of pyrroles were obtained by this method under mild conditions.

Allyltrichlorostannane additions to α-amino aldehydes: Application to the total synthesis of the aspartyl protease inhibitors L-682,679, L-684,414, L-685,434, and L-685,458

The hydroxyethylene dipeptide isosteres L-682,679, L-684,414, L-685,434, and L-685,458 were synthesized in a few steps by a sequence involving an allyltrichlorostannane coupling with an α-amino aldehyde, followed by hydroboration of the corresponding 1,2-

Chiral allylsilane additions to chiral N-Boc-a-amino aldehydes

Addition of chiral allylsilane 4 to chiral W-Boc-α-amino aldehydes in the presence of SnCl2 in CH2Cl2 at -78 °C affords 1,2-syn homoallylic alcohols, potential intermediates for the synthesis of hydroxyethylene peptide isosteres. The diastereoselectivity depends on the aldehyde absolute configuration, with (R)-α-aminoaldehydes (matched case/anti-Felkin addition) exhibiting higher stereoselectivity than its enantiomer (mismatched case/Felkin addition). Thieme Stuttgart.

Diastereoselective addition of allyl reagents to variously N-monoprotected and N,N-diprotected L-alaninals

Diastereoselective C3-elongation processes of N-Boc-, N-Z-, N-Bn-N-Boc-, and N-Bn-N-Z-L-alaninals (Boc = 'BuOCO, Z = PhCH2OCO, Bn = PhCH2) using various allyl reagents, such as allyl bromide in the presence of Zn/aqueous N