64694-19-5

Basic information

• Product Name: 2-ethyl-5-nitrobenzenamine
• Synonyms: 2-ethyl-5-nitrobenzenamine
• CAS NO: 64694-19-5
• Molecular Formula: C₆₂H₆₆O₁₁
• Molecular Weight: 166.1772
• Mol File: 64694-19-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-ethyl-5-nitrobenzenamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ethyl-5-nitrobenzenamine(64694-19-5)
• EPA Substance Registry System: 2-ethyl-5-nitrobenzenamine(64694-19-5)

Safety Data

• Hazardous Substances Data: 64694-19-5(Hazardous Substances Data)

Upstream product

• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 35303-86-7 (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol 
• 104992-64-5 methyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 74666-83-4 1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 35303-87-8 methyl 3-O-acetate-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 100-44-7 benzyl chloride 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl fluoride 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 
• 339276-14-1 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 
• 131531-76-5 p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside 
• 67773-43-7 2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl bromide 

Relevant articles and documents

Ferrocenium complex aided: O-glycosylation of glycosyl halides

A new strategy for the activation of glycosyl halide donors to be utilized in glycosylation reactions is presented, utilizing the ferrocenium (Fc) complexes [FcB(OH)2]SbF6 and FcBF4 as promoters. The scope of the new system has been investigated using glycosyl chloride and glycosyl fluoride donors in combination with common glycosyl acceptors, such as protected glucose. The corresponding glycosylation products were formed in 95 to 10% isolated yields with α/β ratios ranging from 1/1 to β only (2 to 14 h reaction time at room temperature, 40 to 100% ferrocenium promoter load). This journal is

Indolylthio glycosides as effective building blocks for chemical glycosylation

The S-indolyl (SIn) anomeric moiety was investigated as a new leaving group that can be activated for chemical glycosylation under a variety of conditions including thiophilic and metal-assisted pathways. Understanding of the reaction pathways for the SIn moiety activation was achieved via the extended mechanistic study. Also reported is how the new SIn donors fit into selective activation strategies for oligosaccharide synthesis.

A Highly Efficient Glycosidation of Glycosyl Chlorides by Using Cooperative Silver(I) Oxide–Triflic Acid Catalysis

Following our discovery that silver(I) oxide-promoted glycosylation with glycosyl bromides can be greatly accelerated in the presence of catalytic TMSOTf or TfOH, we report herein a new discovery that glycosyl chlorides are even more effective glycosyl do

Reagent Controlled Stereoselective Assembly of α-(1,3)-Glucans

Pre-activation based glycosylations have become a very powerful tool in the assembly of oligosaccharides and the use of nucleophilic additives allows for the in situ generation of reactive intermediates with tailored reactivity. We here use a glycosylation strategy that is based on the use of per-benzylated imidate building blocks for the fully stereoselective construction of a spacer equipped Aspergillus fumigatus α-1,3-octaglucan. We have used the trimethylsilyl iodide (TMSI)-triphenylphosphine oxide (Ph3P=O) for the stereoselective installation of an azidopropanol spacer and triflic acid (TfOH)-dimethyl formamide (DMF) enabled glycosylations for the coupling reactions with the secondary glucosyl C-3-alcohols. An operationally simple in situ activation coupling procedure is introduced and used for the final glycosylation events towards the octasaccharide.

Matching Glycosyl Donor Reactivity to Sulfonate Leaving Group Ability Permits SN2 Glycosylations

Here we demonstrate that highly β-selective glycosylation reactions can be achieved when the electronics of a sulfonyl chloride activator and the reactivity of a glycosyl donor hemiacetal are matched. While these reactions are compatible with the acid- and base-sensitive protecting groups that are commonly used in oligosaccharide synthesis, these protecting groups are not relied upon to control selectivity. Instead, β-selectivity arises from the stereoinversion of an α-glycosyl arylsulfonate in an SN2-like mechanism. Our mechanistic proposal is supported by NMR studies, kinetic isotope effect (KIE) measurements, and DFT calculations.

Reagent Controlled Stereoselective Synthesis of α-Glucans

The development of a general glycosylation method that allows for the stereoselective construction of glycosidic linkages is a tremendous challenge. Because of the differences in steric and electronic properties of the building blocks used, the outcome of

Investigation of Glycosyl Nitrates as Building Blocks for Chemical Glycosylation

Glycosyl nitrates are important synthetic intermediates in the synthesis of 2-amino sugars, 1,2-orthoesters or, more recently, 2-OH glucose. However, glycosyl nitrates have never been glycosidated. Presented herein is our first attempt to use glycosyl nitrates as glycosyl donors for O-glycosylation. Lanthanide triflates showed good affinity to activate the nitrate leaving group.

Iron(iii) chloride-catalyzed activation of glycosyl chlorides

Glycosyl chlorides have historically been activated using harsh conditions and/or toxic stoichiometric promoters. More recently, the Ye and the Jacobsen groups showed that glycosyl chlorides can be activated under organocatalytic conditions. However, thos

Co2(CO)6-propargyl cation mediates glycosylation reaction by using thioglycoside

We discovered that the cobalt-propargyl cation can mediate the glycosylation reaction by activating the thioglycoside donor. The glyco-oxacarbenium cation was formed by transferring the thio-aglycone to the cobalt-propargyl cation that was generated from the cobalt-propargylated acceptor in situ via the activating with Lewis acid. The reactivity of the donor (Armed or dis-armed) and the amount of the Lewis acid control the releasing rate of the cobalt-propargyl group.

O-Benzoxazolyl imidates as versatile glycosyl donors for chemical glycosylation

Herein, we report a new class of glycosyl donors, benzoxazolyl imidates, for chemical glycosylation. The O-benzoxazolyl (OBox) leaving group was designed with an aim to compare the relative reactivity and stability of similarly structured S-benzoxazolyl (