A Synthesis of 2-Acetamido-2,6-dideoxy-D-gulose, 2-Acetamido-2,6-dideoxy-D-idose, and 2,6-Dideoxy-D-xylo-hexose (Boivinose)

1973 ◽  
Vol 51 (18) ◽  
pp. 3039-3043 ◽  
Author(s):  
Malcolm B. Perry ◽  
Virginia Daoust
Keyword(s):  
Catalytic Reduction ◽  
Nef Reaction ◽  
Cellulose Column ◽  
Methanolic Ammonia

The base-catalyzed addition of nitromethane to 5-deoxy-D-xylose gave a mixture of 1,6-dideoxy-1-nitro-D -gulitol (2) and 1,6-dideoxy-1-nitro-D-iditol (3) (ca. 1;1) which underwent the Nef reaction to give 6-deoxy-D-gulose and 6-deoxy-D-idose, Acetylation of mixed 2 and 3 afforded the corresponding 2,3,4,5-tetra-O-acetyl-1,6-dideoxy-1-nitro-D-gulitol (4) and 2,3,4,5-tetra-O-acetyl-1,6-dideoxy-1-nitro-D-iditol (5) derivatives which on treatment with methanolic ammonia yielded 2-acetamido-1,2,6-trideoxy-1-nitro-D-gulitol (11) and 2-acetamido-1,2,6-trideoxy-1-nitro-D-iditol (12) (ca. 6:1). Compounds 11 and 12 underwent the modified Nef reaction to give 2-acetamido-2,6-dideoxy-D-gulose (13) and 2-acetamido-2,6-dideoxy-D-idose (14) which were separated by cellulose column chromatography.Compound 4 was converted to 3,4,5-tri-O-acetyl-1,2,6-trideoxy-1-nitro-D-xylo-hex-1-enitol (6) which on catalytic reduction gave 3,4,5-tri-O-acetyl-1,2,6-trideoxy-1-nitro-D-xylo-hexitol (7). Compound 7 underwent the Nef reaction to yield 2,6-dideoxy-D-xylo-hexose (8) (D-boivinose).

A Synthesis of 2-Amino-2,6-dideoxy-D-(and L-)galaetose (Fucosamine) and 2-Amino-2,6-dideoxy-D-(and L-)talose (Pneumosamine)

1973 ◽  
Vol 51 (6) ◽  
pp. 974-977 ◽  
Author(s):  
Malcolm B. Perry ◽  
Virginia Daoust
Keyword(s):  
Similar Reaction ◽  
Reaction Sequence ◽  
Reaction Conditions ◽  
Nef Reaction ◽  
Methanolic Ammonia

5-Deoxy-D-lyxose underwent base-catalyzed addition with nitromethane to give a mixture of 1,6-dideoxy-1-nitro-D-galactitol and 1,6-dideoxy-1-nitro-D-talitol (ca. 2:1). Acetylation of the crystalline 1,6-dideoxy-1-nitro-D-galactitol gave 2,3,4,5-tetra-O-acetyl-1,6-dideoxy-1-nitro-D-galactitol which on treatment with methanolic ammonia afforded 2-acetamido-1,2,6-trideoxy-1-nitro-D-talitol and 2-acetamido-1,2,6-trideoxy-1-nitro-D-galactitol (ca. 3:1) which under the modified Nef reaction conditions gave 2-acetamido-2,6-dideoxy-D-talose and 2-acetamido-2,6-dideoxy-D-galactose respectively. The glycoses were converted to 2-amino-2,6-dideoxy-D-talose hydrochloride and 2-amino-2,6-dideoxy-D-galactose hydrochloride on hydrolysis with hydrochloric acid.A similar reaction sequence applied to 5-deoxy-L-lyxose afforded the L-enantiomorphic intermediates, and gave 2-amino-2,6-dideoxy-L-talose hydrochloride and 2-amino-2,6-dideoxy-L-galactose hydrochloride as final products.

Synthesis of 2-amino-2-deoxy-D-allose, 2-amino-2-deoxy-D-altrose, and 2-deoxy-D-ribo-hexose from 3,4,5,6-tetraacetoxy-D-ribo-1-nitro-1-hexene

1968 ◽  
Vol 46 (17) ◽  
pp. 2859-2862 ◽  
Author(s):  
M. B. Perry ◽  
Jana Furdová
Keyword(s):  
Nef Reaction ◽  
Methanolic Ammonia

3,4,5,6-Tetraacetoxy-D-ribo-1-nitro-1-hexene with methanolic ammonia afforded a mixture of 2-acetamido-1,2-dideoxy-1-nitro-D-allitol and 2-acetamido-1,2-dideoxy-1-nitro-D-altritol, which were converted via the Nef reaction to 2-acetamido-2-deoxy-D-allose and 2-acetamido-2-deoxy-D-altrose. 2-Amino-2-deoxy-D-allose hydrochloride and 2-amino-2-deoxy-D-altrose hydrochloride were obtained from the 2-acetamido-2-deoxy-glycoses.Reduction of 3,4,5,6-tetraacetoxy-D-ribo-1-nitro-1-hexene afforded 3,4,5,6-tetra-O-acetyl-1,2-dideoxy-1-nitro-D-ribo-hexitol which was converted via the Nef reaction to 2-deoxy-D-ribo-hexose.

THE PREPARATION OF D-RIBOSE-1-C14, D-ARABINOSE-1-C14, AND D-2-DEOXYRIBOSE-1-C14

1959 ◽  
Vol 37 (10) ◽  
pp. 1776-1781 ◽  
Author(s):  
D. H. Murray ◽  
G. C. Butler
Keyword(s):  
Sodium Bicarbonate ◽  
Column Chromatography ◽  
Polar Solvent ◽  
Radiochemical Yield ◽  
Nef Reaction ◽  
Cellulose Column

D-Ribose-1-C14 and D-arabinose-1-C14 have been synthesized by a modified Sowden–Fischer procedure in which the mixed sodium nitropentitols resulting from the condensation of erythrose and C14H3NO2 have been submitted to a Nef reaction. The epimeric labelled pentoses were isolated by cellulose column chromatography in an over-all radiochemical yield of 19%.Mixed nitropentitols-1-C14 have been acetylated, partially deacetylated with sodium bicarbonate in a non-polar solvent, and hydrogenated to yield triacetoxy-1-nitropentane-1-C14. The mixture of this material and the accompanying undeacetylated nitropentitols gave rise, via a Nef reaction, to D-2-deoxyribose-1-C14 (6.3%), D-ribose-1-C14 (3.1%), and D-arabinose-1-C14 (2.9%).

Synthesis of 2-amino-2-deoxy-D-talose and 2-amino-2-deoxy-D-galactose

1968 ◽  
Vol 46 (15) ◽  
pp. 2481-2484 ◽  
Author(s):  
M. B. Perry ◽  
Ann C. Webb
Keyword(s):  
Hydrochloric Acid ◽  
Sodium Methoxide ◽  
Ammonia Solution ◽  
Nef Reaction ◽  
Derivatives Of ◽  
Methanolic Ammonia

Treatment of D-lyxose with nitromethane in the presence of sodium methoxide gave 1-deoxy-1-nitro-D-galactitol which, after conversion to 2,3,4,5,6-penta-O-acetyl-1-deoxy-1-nitro-D-galactitol, reacted with saturated methanolic ammonia solution to yield 2-acetamido-1,2-dideoxy-1-nitro-D-talitol and 2-acetamido-1,2-dideoxy-1-nitro-D-galactitol. 2-Acetamido-1,2-dideoxy-1-nitro-D-talitol and 2-acetamido-1,2-dideoxy-1-nitro-D-galactitol were converted by a modified Nef reaction to 2-acetamido-2-deoxy-D-talose and 2-acetamido-2-deoxy-D-galactose which on hydrolysis with hydrochloric acid afforded 2-amino-2-deoxy-D-talose hydrochloride and 2-amino-2-deoxy-D-galactose hydrochloride. The properties and derivatives of the aminoglycoses are described.

2-Acetamido-2-deoxy-D-glycero-D-gulo-heptose

1969 ◽  
Vol 47 (23) ◽  
pp. 4493-4495 ◽  
Author(s):  
D. T. Williams ◽  
M. B. Perry
Keyword(s):  
Nef Reaction ◽  
Methanolic Ammonia

3,4,5,6,7-Pentaacetoxy-D-gluco-1-nitro-1-heptene with methanolic ammonia afforded crystalline 2-acetamido-1,2-dideoxy-1-nitro-D-glycero-D-gulo-heptitol which was converted via a modified Nef reaction to 2-acetamido-2-deoxy-D-glycero-D-gulo-heptose.

Synthesis of 2-acetamido-2-deoxy-D-gulose, 2-acetamido-2-deoxy-D-idose, and 2-deoxy-D-xylo-hexose from 3,4,5,6-tetraacetoxy-D-xylo-1-nitro-1-hexene

1969 ◽  
Vol 47 (7) ◽  
pp. 1245-1247 ◽  
Author(s):  
M. B. Perry ◽  
Ann C. Webb
Keyword(s):  
Nef Reaction ◽  
Methanolic Ammonia

3,4,5,6-Tetraacetoxy-D-xylo-1-nitro-1-hexene with methanolic ammonia afforded a mixture of 2-acetamido-1,2-dideoxy-1-nitro-D-gulitol and 2-acetamido-1,2-dideoxy-1-nitro-D-iditol which were converted via a Nef reaction to 2-acetamido-2-deoxy-D-gulose and 2-acetamido-2-deoxy-D-idose.Reduction of 3,4,5,6-tetraacetoxy-D-xylo-1-nitro-1-hexene afforded 3,4,5,6-tetra-O-acetyl-1,2-dideoxy-1-nitro-D-xylo-hexitol which was converted via the Nef reaction to 2-deoxy-D-xylo-hexose.

Highly dispersed MnOx–FeOx supported by silicalite-1 for the selective catalytic reduction of NOx with NH3 at low temperatures

2020 ◽  
Vol 10 (16) ◽  
pp. 5525-5534 ◽  
Author(s):  
Jialiang Gu ◽  
Bingjun Zhu ◽  
Rudi Duan ◽  
Yan Chen ◽  
Shaoxin Wang ◽  
...  
Keyword(s):  
Selective Catalytic Reduction ◽  
Low Temperatures ◽  
Catalytic Reduction ◽  
Highly Dispersed ◽  
Reduction Of Nox

MnOx–FeOx-Loaded silicalite-1 catalysts exhibit high NOx conversion at low temperatures.

Transition-metal-free catalytic hydroboration reduction of amides to amines

2020 ◽  
Vol 7 (21) ◽  
pp. 3515-3520
Author(s):  
Wubing Yao ◽  
Jiali Wang ◽  
Aiguo Zhong ◽  
Shiliang Wang ◽  
Yinlin Shao
Keyword(s):  
Transition Metal ◽  
Selective Catalytic Reduction ◽  
Catalytic Reduction ◽  
Value Added ◽  
Metal Free

The selective catalytic reduction of amides to value-added amine products is a desirable but challenging transformation.

Comparative analysis on the effects of diesel particulate filter and selective catalytic reduction systems on a wide spectrum of chemical species emissions

2018 ◽  
Author(s):  
Z. Gerald Liu ◽  
Devin R. Berg ◽  
Thaddeus A. Swor ◽  
James J. Schauer‡
Keyword(s):  
Diesel Engine ◽  
Selective Catalytic Reduction ◽  
Diesel Particulate Filter ◽  
Catalytic Reduction ◽  
Wide Spectrum ◽  
Chemical Species ◽  
Pollutant Emissions ◽  
Particulate Filter ◽  
Diesel Particulate ◽  
Aftertreatment Systems

Two methods, diesel particulate filter (DPF) and selective catalytic reduction (SCR) systems, for controlling diesel emissions have become widely used, either independently or together, for meeting increasingly stringent emissions regulations world-wide. Each of these systems is designed for the reduction of primary pollutant emissions including particulate matter (PM) for the DPF and nitrogen oxides (NOx) for the SCR. However, there have been growing concerns regarding the secondary reactions that these aftertreatment systems may promote involving unregulated species emissions. This study was performed to gain an understanding of the effects that these aftertreatment systems may have on the emission levels of a wide spectrum of chemical species found in diesel engine exhaust. Samples were extracted using a source dilution sampling system designed to collect exhaust samples representative of real-world emissions. Testing was conducted on a heavy-duty diesel engine with no aftertreatment devices to establish a baseline measurement and also on the same engine equipped first with a DPF system and then a SCR system. Each of the samples was analyzed for a wide variety of chemical species, including elemental and organic carbon, metals, ions, n-alkanes, aldehydes, and polycyclic aromatic hydrocarbons, in addition to the primary pollutants, due to the potential risks they pose to the environment and public health. The results show that the DPF and SCR systems were capable of substantially reducing PM and NOx emissions, respectively. Further, each of the systems significantly reduced the emission levels of the unregulated chemical species, while the notable formation of new chemical species was not observed. It is expected that a combination of the two systems in some future engine applications would reduce both primary and secondary emissions significantly.

Effect of Fe on the Selective Catalytic Reduction of NO by NH3 at Low Temperature over Mn/CeO2-TiO2 Catalyst

2012 ◽  
Vol 27 (5) ◽  
pp. 495-500 ◽  
Author(s):  
Da-Wang WU ◽  
Qiu-Lin ZHANG ◽  
Tao LIN ◽  
Mao-Chu GONG ◽  
Yao-Qiang CHEN
Keyword(s):  
Low Temperature ◽  
Selective Catalytic Reduction ◽  
Catalytic Reduction ◽  
Reduction Of No
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