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.

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.

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).

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.

ChemInform Abstract: Concave Reagents. Part 4. Protonation of Nitronate Anions via Concave Pyridines. Stereoselective C-Protonation versus Nef Reaction.

ChemInform ◽  
1990 ◽  
Vol 21 (15) ◽  
Author(s):  
U. LUENING ◽  
R. BAUMSTARK ◽  
M. MUELLER ◽  
C. WANGNICK ◽  
F. SCHILLINGER
Keyword(s):  
Nef Reaction ◽  
Concave Reagents

The NEF Reaction

1955 ◽  
Vol 55 (1) ◽  
pp. 137-155 ◽  
Author(s):  
Wayland E. Noland
Keyword(s):  
Nef Reaction

scholarly journals Cathodic hydrodimerization of nitroolefins

2015 ◽  
Vol 11 ◽  
pp. 1163-1174 ◽  
Author(s):  
Michael Weßling ◽  
Hans J Schäfer
Keyword(s):  
Double Bond ◽  
Nitro Group ◽  
Bond Formation ◽  
Cathodic Reduction ◽  
High Yield ◽  
Easy Access ◽  
Electrolysis Cell ◽  
Aldehydes And Ketones ◽  
Nef Reaction

Nitroalkenes are easily accessible in high variety by condensation of aldehydes with aliphatic nitroalkanes. They belong to the group of activated alkenes that can be hydrodimerized by cathodic reduction. There are many olefins with different electron withdrawing groups used for cathodic hydrodimerization, but not much is known about the behaviour of the nitro group. Synthetic applications of this group could profit from the easy access to nitroolefins in large variety, the C–C bond formation with the introduction of two nitro groups in a 1,4-distance and the conversions of the nitro group by reduction to oximes and amines, the conversion into aldehydes and ketones via the Nef reaction and base catalyzed condensations at the acidic CH bond. Eight 1-aryl-2-nitro-1-propenes have been electrolyzed in an undivided electrolysis cell to afford 2,5-dinitro-3,4-diaryl hexanes in high yield. The 4-methoxy-, 4-trifluoromethyl-, 2-chloro- and 2,6-difluorophenyl group and furthermore the 2-furyl and 2-pyrrolyl group have been applied. The reaction is chemoselective as only the double bond but not the nitro group undergoes reaction, is regioselective as a ß,ß-coupling with regard to the nitro group and forms preferentially two out of six possible diastereomers as major products.

Nef reaction

2009 ◽  
pp. 387-388
Author(s):  
Jie Jack Li
Keyword(s):  
Nef Reaction

Nef reaction

2003 ◽  
pp. 282-282
Author(s):  
Jie Jack Li
Keyword(s):  
Nef Reaction
Sign in / Sign up

Export Citation Format

Share Document