61404-93-1

Upstream product

• 34461-00-2 nitromalondialdehyde sodium salt 
• 100-61-8 N-methylaniline 
• 75-52-5 nitromethane 
• 122-51-0 orthoformic acid triethyl ester 
• 120539-85-7 ((E)-2-Nitro-vinylsulfanyl)-benzene 

Downstream Products

• 1346595-69-4 [(4-methoxyphenyl)methyl][(Z)-2-nitroethenyl]amine 

Relevant academic research and scientific papers

Novel synthesis method of oseltamivir

The invention provides a novel synthesis method of oseltamivir. The synthesis method comprises the following steps: taking a compound (E)-2-(2-nitrovinyl) isoindoline-1,3-diketone and ethyl pyruvate as initial raw materials, and carrying out Michael addition reaction under the condition of catalysis of a thiourea catalyst to obtain a corresponding Michael addition product; then, subjecting the Michael addition product and (formyl methylene) triphenyl phosphine to a Wittig reaction and a Henry reaction in a pot so as to obtain a ring closing product; and forming an etherified product from the ring closing product and a trichloroacetonitrile intermediate, and performing reduction, acetylation and de-protection to obtain oseltamivir. The reaction route comprises six steps, raw materials used in each step of reaction are easy to obtain and not expensive, the operation is easy, the yield of each step of reaction is high, no heavy metal or azide is used in the whole synthesis process, and the method is green and safe and can be applied to industrial production.

Akt inhibitor intermediate SM1 and preparation method thereof

The invention discloses an Akt inhibitor intermediate SM1 and a preparation method thereof. The Akt inhibitor intermediate SM1 is obtained by reacting a compound IM1 with p-toluenesulfonic acid. The preparation method of the compound IM1 comprises the following steps: (1) reacting a compound 4 with a compound 9 under the actions of a pyrrolidine catalyst and benzoic acid, adding trifluoroacetic acid after reaction is finished, adding alkali after reaction is finished, and extracting to obtain a solution of a compound 10; (2) reacting the solution of the compound 10 with the trifluoroacetic acid and triethyl silicane, adding alkali after reaction is finished, extracting to obtain a solution of an intermediate, and reacting the intermediate with Boc anhydride under the effect of alkali to obtain a compound 11; and (3) under the effect of a reducing agent on the compound II, obtaining the compound IM1. The provided intermediate SM1 is solid, is convenient to weigh and convenient to store,and is easily refined, the shortcoming that in the prior art, IM1 is liquid and is difficult to refine is overcome, and a quality control standard of SM1 is easy to establish on production.

Stereoisomers of oseltamivir-synthesis, in silico prediction and biological evaluation

Oseltamivir is an important antiviral drug, which possess three chirality centers in its structure. From eight possible stereoisomers, only two have been synthesized and evaluated so far. We describe herein the stereoselective synthesis, computational activity prediction and biological testing of another three diastereoisomers of oseltamivir. These isomers have been synthesized using stereoselective organocatalytic Michael addition, cyclization and reduction. Their binding to viral neuraminidase N1 of influenza A virus was evaluated by quantum-chemical calculations and their anti-influenza activities were tested by an in vitro virus-inhibition assay. All three isomers displayed antiviral activity lower than that of oseltamivir, however, one of the stereoisomers, (3S,4R,5S)-isomer, of oseltamivir showed in vitro potency towards the Tamiflu-sensitive influenza viral strain A/Perth/265/2009(H5N1) comparable to Tamiflu.

Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael–Henry cascade reactions

The thiourea-catalyzed asymmetric synthesis of highly enantioenriched spirocyclopentaneoxindoles containing chiral amide functional groups using simple 3-substituted oxindoles and nitrovinylacetamide as starting materials was achieved successfully. This protocol features operational simplicity, high atom economy, and high catalytic asymmetry, thus representing a versatile approach to the synthesis of highly enantioenriched spirocyclopentaneoxindoles.

Organocatalytic michael addition of aldehydes to protected 2-amino-1-nitroethenes: The practical syntheses of oseltamivir (tamiflu) and substituted 3-aminopyrrolidines

Figure Presented Hey Mickey, you're so fine! Organocatalytic Michael additions of aldehydes with protected 2-amino-1-nitroethene could go through three different transition-states to afford adducts with usual and unusual stereochemistry, thereby providing a facile entry to Tamiflu (see scheme) and substituted 3-aminopyrrolidines. TMS = trimethylsilyl, Ac = acetyl.

A Facile Method for the Preparation of Nitroenamines

Various kinds of nitroenamines are readily prepared by the reaction of 1-nitro-2-phenylthioalkenes with amines.