117136-22-8

Upstream product

• 100-39-0 benzyl bromide 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 75-05-8 acetonitrile 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 83-87-4 D-glucose pentaacetate 
• 13265-84-4 D-glucal 

Downstream Products

• 117136-24-0 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1β-(2'-dithianyl)-2-nitro-D-glucitol 
• 117153-47-6 ethyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranoside 
• 444666-51-7 dimethyl (3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranosyl)malonate 
• 671792-63-5 methyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranosyl)-L-lactate 
• 671792-64-6 tert-butyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranosyl)-D-lactate 
• 671792-61-3 tert-butyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-glucopyranosyl)-D-lactate 
• 698371-42-5 phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-1-thio-β-D-glucopyranoside 
• 671792-69-1 (3R,4aS,6R,7S,8R,8aR)-7,8-bis-benzyloxy-6-benzyloxymethyl-3-methyl-hexahydro-pyrano[2,3-b][1,4]oxazin-2-one 
• 1160638-22-1 methyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranoside 
• 1160638-16-3 methyl 2,3,4-tri-O-benzyl-6-O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 1160638-23-2 (2-trimethylsilyl)ethyl 3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranoside 
• 1240492-59-4 C₃₂H₃₃NO₁₀ 
• 1240492-58-3 C₃₂H₃₃NO₁₀ 

Relevant academic research and scientific papers

N-heterocyclic carbene catalyzed C-glycosylation: A concise approach from stetter reaction

Described herein is the first example of an organocatalytic approach for acylanion addition to the anomeric carbon of 2-nitroglucal using an N-heterocyclic carbene catalyst. Control over the reaction conditions gives β-selective and nitro-eliminated C-glycosides, providing opportunities to produce new classes of C-glycoside.

Synthesis of 2-nitroglycals from glycals using the tetrabutylammonium nitrate-trifluoroacetic anhydride-triethylamine reagent system and base-catalyzed ferrier rearrangement of acetylated 2-nitroglycals

A reagent system comprising tetrabutylammonium nitrate-trifluoroacetic anhydride-triethylamine has been developed for the synthesis of 2-nitroglycals from various protected glycals. The base-catalyzed Ferrier rearrangement on tri-O-acetylated 2-nitroglycals has been reported for the first time. Reactivity of these nitroacetates and associated selectivity has been examined, and some of the products have been converted into 2,3-diamino-2,3-dideoxyglycosides and methyl N-acetyl-d-lividosaminide.

Acetyl chloride - Silver nitrate - Acetonitrile: A reagent system for the synthesis of 2-nitroglycals and 2-nitro-1-acetamido sugars from glycals

A new reagent system comprising acetyl chloride, silver nitrate, and acetonitrile has been developed for the synthesis of 2-nitroglycals from the corresponding glycals. Under certain conditions, the formation of 2-nitro-1-acetamido sugars has also been observed. In addition, a few other non-carbohydrate-derived olefins also gave the corrresponding conjugated nitroolefins.

2-NITROGLYCALS - PREPARATION AND NUCLEOPHILIC ADDITION REACTIONS

2-Nitroglycals were prepared by reaction of the corresponding glycals with nitronium tetrafluoroborate and base.The stereoselective Michael addition reactions of O-alkyl-2-nitroglucals with a number of nucleophiles are described.