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

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

Uses

Used in Pharmaceutical Industry:
(+)-Alexine is used as a potential treatment for neurodegenerative diseases such as Alzheimer's due to its ability to inhibit acetylcholinesterase, thereby potentially slowing cognitive decline.
Used in Pest Control Industry:
(+)-Alexine is used as an insecticide for its capacity to disrupt the nervous system of insects, offering an alternative for pest management.
Used in Oncology Research:
(+)-Alexine is used as a subject of interest in anti-cancer drug development due to its demonstrated anti-cancer properties, which may contribute to the creation of novel therapeutic agents.
Used in Inflammation Management Research:
(+)-Alexine is used in the study of anti-inflammatory agents, as its anti-inflammatory properties could lead to the development of new treatments for inflammatory conditions.

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

• 121588-54-3 (1R,5S,6R,7R,9S,10R)-5-(tert-Butyl-dimethyl-silanyloxy)-9-methoxy-8-oxa-2-aza-tricyclo[5.2.1.0^2,6]decan-10-ol 
• 312515-07-4 (1S,5R,6R,7R,7aS)-6,7-Bis-benzyloxy-5-hydroxymethyl-hexahydro-pyrrolizin-1-ol 
• 312515-13-2 (3S,4R,5S)-3,4-Bis-benzyloxy-5-((S)-1-hydroxy-but-3-enyl)-pyrrolidin-2-one 
• 312515-17-6 (S)-3-((2S,3R,4S)-3,4-Bis-benzyloxy-5-oxo-pyrrolidin-2-yl)-3-methoxymethoxy-propionaldehyde 
• 1054655-54-7 (3S,4R,5S)-3,4-Bis-benzyloxy-5-((S)-3-hydroxy-1-methoxymethoxy-propyl)-pyrrolidin-2-one 
• 312514-97-9 (3S,4R,5S)-3,4-Bis-benzyloxy-5-((S)-1-methoxymethoxy-but-3-enyl)-pyrrolidin-2-one 
• 312515-15-4 (3S,4R,5S)-3,4-Bis-benzyloxy-5-((S)-3,4-dihydroxy-1-methoxymethoxy-butyl)-pyrrolidin-2-one 
• 312514-95-7 (3S,4R,5S)-3,4-Bis-benzyloxy-5-((S)-1-hydroxy-but-3-enyl)-1-(4-methoxy-benzyl)-pyrrolidin-2-one 
• 312515-22-3 (2S,3R,4R,5R)-3,4-Bis-benzyloxy-2-((S)-3-hydroxy-1-methoxymethoxy-propyl)-5-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 312515-29-0 (3S,4R,5S)-3,4-Bis-benzyloxy-5-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-1-methoxymethoxy-propyl]-pyrrolidin-2-one 
• 98260-64-1 methyl 2-azido-3-O-benzyl-2-deoxy-α-D-mannofuranoside 
• 121588-48-5 methyl N-benzyl-3-O-benzyl-2,5-dideoxy-2,5-imino-β-L-gulofuranoside 
• 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 
• 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 

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 Syntheses of (-)-7- epi -Alexine and (+)-Alexine Using Stereoselective Allylation

Total syntheses of (-)-7- epi -alexine and (+)-alexine were achieved by using stereoselective allylation via a functionalized pyrrolidine obtained from an extended chiral 1,3-oxazine. The synthetic strategies include pyrrolidine formation via oxazine cleavage and diastereoselective allylations of a pyrrolidine aldehyde. (-)-7- epi -Alexine and (+)-alexine were synthesized from anti, syn, anti -oxazine in 12 steps.

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.

New asymmetric strategy for the total synthesis of naturally occurring (+)-alexine and (-)-7-epi-alexine

A novel and highly convenient process is described for the asymmetric synthesis of polyhydroxylated pyrrolizidine alkaloids, (+)-alexine [(1R,2R,3R,7S,7aS)-3-hydroxymethyl-1,2,7-trihydroxypyrrolizidine] and (-)-7-epi-alexine [(1R,2R,3R,7R,7aS)-3-hydroxymethyl-1,2,7-trihydroxypyrrolizidine], as the potent glycosidase inhibitors by featuring the efficient and stereodefined elaboration of the functionalized pyrrolidine derivatives, which were, in turn, prepared via stereoselective manipulation of the homochiral allyl alcohol precursors derived from l-xylose.

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