116174-63-1

Basic information

• Product Name: (+)-Alexine
• Synonyms: (+)-Alexine;(1R,7aS)-Hexahydro-3β-(hydroxymethyl)-1H-pyrrolizine-1β,2α,7α-triol;(1R,7aα)-3β-(Hydroxymethyl)hexahydro-1H-pyrrolizine-1β,2α,7α-triol;Alexine
• CAS NO: 116174-63-1
• Molecular Formula: C8H15NO4
• Molecular Weight: 189.209
• Mol File: 116174-63-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 417.4°C at 760 mmHg
• Flash Point: 263.5°C
• Appearance: /
• Density: 1.53g/cm³
• Vapor Pressure: 1.03E-08mmHg at 25°C
• Refractive Index: 1.647
• CAS DataBase Reference: (+)-Alexine(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Alexine(116174-63-1)
• EPA Substance Registry System: (+)-Alexine(116174-63-1)

Safety Data

• Hazardous Substances Data: 116174-63-1(Hazardous Substances Data)

Usage

General Description

(+)-Alexine is a chemical compound that has been identified as a potent inhibitor of acetylcholinesterase, an enzyme that plays a key role in the breakdown of neurotransmitters in the central nervous system. As a result, (+)-Alexine has been studied for its potential use in the treatment of neurodegenerative diseases such as Alzheimer's. Additionally, it has also shown potential as an insecticide due to its ability to disrupt the nervous system of insects. Recent research has also suggested that (+)-Alexine may have anti-inflammatory and anti-cancer properties, making it a subject of interest for future drug development.

InChI:InChI=1/C8H15NO4/c10-3-4-7(12)8(13)6-5(11)1-2-9(4)6/h4-8,10-13H,1-3H2/t4-,5+,6+,7-,8-/m1/s1

Upstream product

• 312515-07-4 (1S,5R,6R,7R,7aS)-6,7-Bis-benzyloxy-5-hydroxymethyl-hexahydro-pyrrolizin-1-ol 
• 1032326-03-6 (1R,2R,3R,7S,7aS)-1,7-bis(benzyloxy)hexahydro-3-(hydroxymethyl)-1H-pyrrolizin-2-ol-N-oxide 
• 1032326-06-9 (1R,2R,3R,7S,7aS)-1,7-bis(benzyloxy)hexahydro-3-(hydroxymethyl)-1H-pyrrolizin-2-ol 
• 121588-47-4 (1R,3S,4R,6S,7R)-5-Benzyl-7-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxy-2-oxa-5-aza-bicyclo[2.2.1]heptane 
• 121588-46-3 (R)-1-((2R,3R,4S,5S)-4-Azido-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethanol 

Relevant articles and documents

Enantioselective synthesis of: Anti -3-alkenyl-2-amido-3-hydroxy esters: Application to the total synthesis of (+)-alexine

A straightforward synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters from the corresponding racemic α-amino-β-keto esters by using a ATH/DKR protocol has been developed. This method gives moderate to excellent yields with high chemo-, diastereo- and enantioselectivities for a broad range of substrates. In order to highlight the versatility of the methodology it was applied in an efficient asymmetric synthesis of the polyhydroxylated pyrrolizidine alkaloid (+)-alexine.

Total synthesis of (+)-alexine by utilizing a highly stereoselective [3+2] annulation reaction of an TV-tosyl-α-amino aldehyde and a 1,3-bis(silyl)propene

A novel route towards the polyhydroxylated pyrrolizidine alkaloid (+)-alexine has been developed. A key step in this synthesis is a highly stereoselective [3+2] annulation reaction of N-Ts-α-amino aldehyde 7a (Ts=tosyl) and 1,3-bis(silyl)propene 8a for the construction of the polyhydroxylated pyrrolidine subunit of the target molecule. Previous synthetic strategies rely on carbohydrates that require several protecting-group manipulations, there-by making the total number of steps relatively high. The [3+2] annulation strategy compares favorably with carbohydrate-based syntheses and constitutes a highly efficient entry to polyhydroxylated alkaloids.

Asymmetric total synthesis of natural pyrrolizidine alkaloid, (+)-alexine

The total synthesis of the potent glycosidase inhibitor (+)-alexine with five contiguous stereogenic centres [(1R,2R,3R,7S,7aS)-3-hydroxymethyl-1,2,7-trihydroxypyrrolizidine alkaloid] is described featuring the efficient and stereodefined novel elaboratio