161024-43-7

Basic information

• Product Name: (-)-Lentiginosine
• Synonyms: 1,2-Indolizinediol,octahydro-, [1S-(1a,2b,8aa)]-; (+)-Lentiginosine;(1S,2S,8aS)-1,2-Dihydroxyindolizidine; (1S,2S,8aS)-Lentiginosine; Lentiginosine
• CAS NO: 161024-43-7
• Molecular Formula: C8H15NO2
• Molecular Weight: 157.212
• Product Categories: pharmacetical
• Mol File: 161024-43-7.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 287.4°Cat760mmHg
• Flash Point: 154.4°C
• Appearance: /
• Density: 1.23g/cm³
• Vapor Pressure: 0.00028mmHg at 25°C
• Refractive Index: 1.572
• CAS DataBase Reference: (-)-Lentiginosine(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Lentiginosine(161024-43-7)
• EPA Substance Registry System: (-)-Lentiginosine(161024-43-7)

Safety Data

• Hazardous Substances Data: 161024-43-7(Hazardous Substances Data)

Usage

Description

(-)-Lentiginosine is a tetrahydroisoquinoline alkaloid derived from the plant Psychotria lentiginosa. It features a unique chemical structure with a benzylisoquinoline core, a cyclopropane ring, and an unsaturated lactone group. This natural product has demonstrated potential biological activities such as anti-inflammatory, antioxidant, and cytotoxic properties, positioning it as a promising candidate for pharmaceutical and medical research and applications.
Used in Pharmaceutical Industry:
(-)-Lentiginosine is used as a drug development candidate for its potential to treat various diseases due to its anti-inflammatory, antioxidant, and cytotoxic properties.
Used in Medical Research:
(-)-Lentiginosine is used as a subject of study for its potential biological activities, which include anti-inflammatory, antioxidant, and cytotoxic effects, making it a valuable target for further research in the medical field.

InChI:InChI=1/C8H15NO2/c10-7-5-9-4-2-1-3-6(9)8(7)11/h6-8,10-11H,1-5H2/t6-,7-,8-/m0/s1

Upstream product

• 160208-49-1 (1S,2S,8aS)-1,2-Bis<(tert-butyldiphenylsilyl)oxy>octahydroindolizine 
• 152189-97-4 (1S,2R,8aS)-hexahydro-1,2-dihydroxyindolizin-3(5H)-one 
• 166533-28-4 (1S,2S,8aS)-1,2-Bis(methoxymethoxy)indolizidine 
• 203730-34-1 (2S,3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2-[4-(toluene-4-sulfonyloxy)-butyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 181121-96-0 (1S,2S,8aS)-1,2-bis(tert-butoxy)octahydroindolizine 
• 367252-00-4 (1S,2R,8aS)-1,2-diacetyloxy-1,2,3,5,8,8a-hexahydro-3-indolizinone 
• 444988-76-5 (1S,2S,8aS)-1-benzyloxy-2-hydroxy-indolizidine 
• 501939-10-2 (1S,2S,8aS)-(-)-1,2-dihydroxy-1,2,3,5,8,8a-hexahydroindolizine 
• 952057-08-8 C₁₂H₁₇NO₅ 
• 952057-02-2 C₂₈H₃₃NO₆S₂Si 
• 952057-03-3 C₃₀H₃₇NO₇S₂Si 
• 952057-04-4 C₃₄H₃₉NO₅S₃Si 
• 952057-05-5 C₃₁H₃₃NO₆SSi 
• 617700-43-3 Carbamic acid (E)-(S)-3-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-1-ethyl-allyl ester 

Relevant articles and documents

Stereoselective addition of Grignard reagents to sulfinimines derived from tartrate diol (threitol): Generation of chiral building blocks for the collective total synthesis of lentiginosine, conhydrine and methyldihydropalustramate

A systematic investigation of the addition of Grignard reagents to sulfinimines derived from tartaric acid diol was undertaken. It was observed that the chirality of the inherent tartrate moiety influences the diastereoselectivity of the resultant sulfinamides formed in the reaction. The formed products serve as excellent building blocks for the synthesis of natural products. This has been demonstrated in the collective total synthesis of lentiginosine, (+)-α-conhydrine and methyldihydropalustramate.

Asymmetric synthesis of (+)-lentiginosine using a chiral aziridine based approach

The synthesis of the indolizidine alkaloid, (+)-lentiginosine, is described. A key feature of the preparative route is the efficient and stereoselective construction of a dihydroxylated pyrrolidine via Sharpless asymmetric dihydroxylation of an aziridine-

Practical synthesis of trans-dihydroxybutyrolactols as chiral C4 building blocks and their application to the synthesis of polyhydroxylated alkaloids

Practical syntheses of trans-dihydroxybutyrolactols 2a, 2b and 2c from inexpensive chiral pool compounds l-ascorbic, d- and l-tartaric acid have been achieved on a multigram-scale. The synthetic applications of these chiral building blocks have been demonstrated in the efficient total or formal synthesis of polyhydroxylated alkaloids (+)-lentiginosine and (-)-deacetylanisomycin in concise routes. The Royal Society of Chemistry 2013.