Browse
Submit Data
Databases
API
Help

Dataset Information

223 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Facile preparation of a highly functionalized tetrahydropyran by catalytic hydrogenation of an oxazoline.

ABSTRACT: 2-Amino-1,5-anhydro-2-deoxy-D-glucitol, a highly functionalized tetrahydropyran, is a versatile building unit in many natural products. A facile route to this type of synthetic building unit from the corresponding 2-aminopyranoses, as exemplified by an application to D-glucosamine, is outlined. A simple catalytic hydrogenation at C-1 of an oxazoline constructed from the corresponding 2-aminopyranose results in the desired product.

SUBMITTER: Hesek D

PROVIDER: S-EPMC2846112 | biostudies-literature | 2008 Sep

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Facile preparation of a highly functionalized tetrahydropyran by catalytic hydrogenation of an oxazoline.

Hesek Dusan D Lee Mijoon M Yamaguchi Takao T Noll Bruce C BC Mobashery Shahriar S

The Journal of organic chemistry 20080809 18

2-Amino-1,5-anhydro-2-deoxy-D-glucitol, a highly functionalized tetrahydropyran, is a versatile building unit in many natural products. A facile route to this type of synthetic building unit from the corresponding 2-aminopyranoses, as exemplified by an application to D-glucosamine, is outlined. A simple catalytic hydrogenation at C-1 of an oxazoline constructed from the corresponding 2-aminopyranose results in the desired product. ...[more]

PMID: 18690743

Similar Datasets

Facile synthesis of highly functionalized ethyltrifluoroborates.

Project description:Organotrifluoroborates are generating increased interest because of their ease of preparation and purification and indefinite shelf life. Herein we report the preparation of organotrifluoroborates bearing functional groups that can be manipulated at different stages of the synthetic route, exploiting the inertness of their carbon-boron bonds. The alkylation of 2,2-dicyanoethyltrifluoroborate with a variety of electrophiles and of (EWG)2CH2 with potassium iodomethyltrifluoroborate resulted in di- and trisubstituted ethyltrifluoroborates in good to excellent yields.

| S-EPMC2504466 | biostudies-literature

Preparation and Enhanced Catalytic Hydrogenation Activity of Sb/Palygorskite (PAL) Nanoparticles.

Project description:A Sb/palygorskite (PAL) composite was synthesized by a facile solvothermal process and applied in catalytic hydrogenation of p-nitrophenol for the first time. It was found that the Sb nanoparticles with the sizes of 2-5 nm were well dispersed on the fiber of PAL, while partial aggregated Sb nanoparticles with sizes smaller than 200 nm were also loaded on the PAL. The Sb/PAL composite with 9.7% Sb mass amounts showed outstanding catalytic performance by raising the p-nitrophenol conversion rate to 88.3% within 5 min, which was attributed to the synergistical effect of Sb and PAL nanoparticles facilitating the adsorption and catalytic hydrogenation of p-nitrophenol.

| S-EPMC5515725 | biostudies-literature

An efficient and facile access to highly functionalized pyrrole derivatives.

Project description:A straightforward and one-pot synthesis of pyrrolo[3,4-c]pyrrole-1,3-diones via Ag(I)-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with N-alkyl maleimide, followed by readily complete oxidation with DDQ, has been successfully developed. Further transformation with alkylamine/sodium alkoxide alcohol solution conveniently afforded novel polysubstituted pyrroles in good to excellent yields. This methodology for highly functionalized pyrroles performed well over a broad scope of substrates. It is conceivable that this efficient construction method for privileged pyrrole scaffolds could deliver more active compounds for medicinal chemistry research.

| S-EPMC5942380 | biostudies-literature

Facile preparation of Cu-Fe oxide nanoplates for ammonia borane decomposition and tandem nitroarene hydrogenation.

Project description:A facile substrate involved strategy was used to prepare Cu-Fe LDO (layered double oxide) nanoplates. The material exhibited good-efficiency for decomposition of ammonia borane (AB) in alkaline methanol solution. Significantly, the material also demonstrated excellent catalytic performance in the reduction of various nitroarenes by coupling with AB hydrolysis in a one pot tandem reaction, and gave excellent yields of the corresponding amine products.

| S-EPMC9040926 | biostudies-literature

Catalytic Nanoassemblies Formed by Short Peptides Promote Highly Enantioselective Transfer Hydrogenation.

Project description:Self-assembly enables formation of incredibly diverse supramolecular structures with practically important functions from simple and inexpensive building blocks. Here, we show how a semirational, bottom-up approach to create emerging properties can be extended to a design of highly enantioselective catalytic nanoassemblies. The designed peptides comprising as few as two amino acid residues spontaneously self-assemble in the presence of metal ions to form supramolecular, vesicle-like nanoassemblies that promote transfer hydrogenation of ketones in an aqueous phase with excellent conversion rates and enantioselectivities (>90% ee).

| S-EPMC7235949 | biostudies-literature

A comparison between oxazoline-imidazolinylidene, -imidazolylidine, -benzimidazolylidene hydrogenation catalysts.

Project description:Imidazolinylidene, imidazolylidine, benzimidazolylidene complexes 1a-c were prepared and tested in asymmetric hydrogenations of a series of largely unfunctionalized alkenes. Similarities and differences in the catalytic performance of these complexes were rationalized in terms of the predicted mechanisms of these reactions, and their relative tendencies to generate protons under the hydrogenation conditions.

| S-EPMC3826777 | biostudies-literature

Facile and efficient preparation of anisotropic DNA-functionalized gold nanoparticles and their regioselective assembly.

Project description:Anisotropic nanoparticles can provide considerable opportunities for assembly of nanomaterials with unique structures and properties. However, most reported anisotropic nanoparticles are either difficult to prepare or to functionalize. Here we report a facile one-step solution-based method to prepare anisotropic DNA-functionalized gold nanoparticles (a-DNA-AuNP) with 96% yield and with high DNA density (120 ± 20 strands on the gold hemisphere). The method is based on the competition between a thiolated hydrophilic DNA and a thiolated hydrophobic phospholipid and has been applied to prepare a-DNA-AuNPs of different sizes and with a variety of DNA sequences. In addition, DNA strands on the a-DNA-AuNPs can be exchanged with other DNA strands with a different sequence. The anisotropic nature of the a-DNA-AuNPs allows regioselective hetero- and homonuclear assembly with high monodispersity, as well as regioselective functionalization of two different DNA strands for more diverse applications.

| S-EPMC3902043 | biostudies-literature

Construction of highly functionalized diazoacetoacetates via catalytic Mukaiyama-Michael reactions.

Project description:Functionalized diazo acetoacetates are prepared by an efficient Mukaiyama-Michael reaction between methyl 3-(trialkylsilanoxy)-2-diazo-3-butenoate and alpha,beta-unsaturated enones. Vinyl ether and ketone derivatives are both accessible in good to excellent yield through this methodology. The mild Lewis acid zinc(II) triflate is the optimal catalyst, and its loading can be as low as 0.1 mol %. In addition, zinc triflate was also found to be a superior catalyst for the related Mukaiyama-aldol reaction.

| S-EPMC3119889 | biostudies-literature

Facile access to functionalized chiral secondary benzylic boronic esters <i>via</i> catalytic asymmetric hydroboration.

Project description:Allylic and homoallylic phosphonates bearing an aryl or heteroaryl substituent at the γ- or δ-position undergo rhodium-catalyzed asymmetric hydroboration by pinacolborane to give functionalized chiral secondary benzylic boronic esters in yields up to 86% and enantiomer ratios up to 99 : 1. Compared to minimally-functionalized terminal and 1,1-disubstituted vinyl arenes, there are relatively few reports of efficient catalytic asymmetric hydroboration (CAHB) of more highly functionalized internal alkenes. Phosphonate substrates bearing a variety of common heterocyclic ring systems, including furan, indole, pyrrole and thiophene derivatives, as well as those bearing basic nitrogen substituents (e.g., morpholine and pyrazine) are tolerated, although donor substituents positioned in close proximity of the alkene can influence the course of the reaction. Stereoisomeric (E)- and (Z)-substrates afford the same major enantiomer of the borated product. Deuterium-labelling studies reveal that rapid (Z)- to (E)-alkene isomerization accounts for the observed (E/Z)-stereoconvergence during CAHB. The synthetic utility of the chiral boronic ester products is illustrated by stereospecific C-B bond transformations including stereoretentive electrophile promoted 1,2-B-to-C migrations, stereoinvertive SE2 reactions of boron-ate complexes with electrophiles, and stereoretentive palladium- and rhodium-catalyzed cross-coupling protocols.

| S-EPMC6520923 | biostudies-literature

Phosphine-promoted [3 + 3] annulations of aziridines with allenoates: facile entry into highly functionalized tetrahydropyridines.

Project description:The phosphine-mediated [3 + 3] annulations of aziridines and allenes are experimentally simple reactions, run under very mild conditions, for the preparation of highly functionalized tetrahydropyridines in yields of up to 98% and trans/cis ratios of up to 97:3. In addition to steps that are typical of nucleophilic phosphine-catalyzed reactions of allenoates, the mechanism of this new reaction features apparent nucleophilic aromatic substitution and concomitant desulfonylation, processes hitherto unknown during phosphine-promoted cycloaddition reactions. Notably, these reactions are the first reported examples of aziridines as reaction partners in nucleophilic phosphine-catalyzed transformations.

| S-EPMC2749062 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data