121104-76-5

Usage

Chemical structure

A chemical compound containing an indolizine core with four hydroxyl groups and a benzoate moiety.

Stereochemistry

The compound has a stereochemistry of 1S,6S,7S,8R,8aR, which refers to the three-dimensional arrangement of the atoms in the molecule.

Indolizine ring system

It is a derivative of the indolizine ring system, which is a tricyclic, unsaturated heterocyclic organic compound.

Tetrahydro derivative

It is a tetrahydro derivative of indolizine, which means that it has four hydrogen atoms added to the indolizine ring system.

Potential applications

The compound may have potential applications in pharmaceuticals or other industries due to the unique properties of the indolizine ring system and the presence of the benzoate group.

Further research

Further research and testing may be needed to fully understand the potential uses and properties of 1,6,7,8-Indolizinetetrol, octahydro-, 6-benzoate, (1S,6S,7S,8R,8aR)-.

InChI:InChI=1/C15H19NO5/c17-10-6-7-16-8-11(13(18)14(19)12(10)16)21-15(20)9-4-2-1-3-5-9/h1-5,10-14,17-19H,6-8H2/t10-,11-,12+,13+,14+/m0/s1

Upstream product

• 130446-97-8 6-O-benzoyl-1,8-O-isopropyidenecastanospermine 
• 79831-76-8 (1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine 
• 98-88-4 benzoyl chloride 
• 130446-90-1 6,7-di-O-benzoyl-1,8-O-isopropylidenylcastanospermine hydrochloride 
• 130549-04-1 6,7-di-O-benzoylcastanospermine hydrochloride 
• 130446-91-2 1,8-O-isopropylidenylcastanospermine 

Downstream Products

• 156206-13-2 7-O-t-butyldimethylsilyl-1,8-O-cyclohexylidenecastanospermine 
• 156257-98-6 7-O-t-butyldimethylsilyl-1,8-O-cyclohexylidene-6-epicastanospermine 
• 156206-12-1 6-O-benzoyl-7-O-t-butyldimethylsilyl-1,8-O-cyclohexylidenecastanospermine 
• 156205-97-9 6-amino-6-N-benzyl-1,8-O-cyclohexylidene-6-deoxy-7-O-methoxymethylcastanospermine 
• 156205-92-4 1,8-O-cyclohexylidene-6-O-methanesulfonyl-7-O-methoxymethylcastanospermine 
• 156205-94-6 6-azido-1,8-O-cyclohexylidene-6-deoxy-7-O-methoxymethylcastanospermine 
• 156205-89-9 1,8-O-isopropylidene-6-O-methanesulfonyl-7-O-methoxymethylcastanospermine 
• 156205-98-0 6-amino-1,8-O-cyclohexylidene-6-deoxy-6-N-bis(2'-hydroxyethyl)-7-O-methoxymethylcastanospermine 
• 156206-06-3 1,8-cyclohexylidene-6-epi-7-O-methoxymethyl-6-C-vinylcastanospermine 
• 156205-93-5 6-azido-6-deoxy-1,8-O-isopropylidene-7-O-methoxymethylcastanospermine 
• 156206-16-5 6-N-benzylacetamino-6-deoxycastanospermine 
• 156206-11-0 1,8-O-cyclohexylidene-6-deoxy-7-O-methoxymethyl-6-C-vinylcastanospermine 
• 156205-99-1 6-amino-6-N-butyl-1,8-O-cyclohexylidene-6-deoxy-6-N-ethyl-7-O-methoxymethylcastanospermine 
• 156206-04-1 6-O-butyl-1,8-O-cyclohexylidene-7-O-methoxymethylcastanospermine 

Relevant academic research and scientific papers

A FACILE SELECTIVE ACYLATION OF CASTANOSPERMINE

A facile selective acylation on the 6-hydroxyl group of the polyhydroxylated indolizidine alkaloid castanospermine, (1), has been achieved by the in situ use of a preformed dibutyl organotin derivative.

PROCESS FOR PREPARING 6-O-MONOESTERS OF CASTANOSPERMINE

The present invention relates to a process for preparing a compound of formula (I), wherein R is C1-C10 alkyl, phenyl or substituted phenyl, comprising treating a compound of formula (II), with bis(tributyltin) oxide in an organic solvent selected from the group consisting of o-xylene, m-xylene, p-xylene and mixed xylenes; and subsequently treating the reaction mixture with a compound of formula (III), wherein X is halogen and R is defined as above.

Combinations of retroviral inhibitors

The combination of compounds of formula I and II can be used for the treatment of retroviraI infections. The combination can be used to treat AIDS and ARC and other diseases caused by the retrovirus HTV or other related viruses.

The Chemistry of Castanospermine, Part IV1: Synthetic Modifications at C-8

New methods for the selective functionalisation of castanospermine has enabled the synthesis of analogues and derivatives selectively modified at C-8.

The Chemistry of Castanospermine, Part I: Synthetic Modifications at C-6

Methodology for the selective functionalisation of castanospermine is outlined which has allowed the synthesis of a number of analogues selectively modified at C-6.Australine and some australine analugues have also been synthesized from castanospermine.

Esters of castanospermine in the treatment of cerebral malaria

Red blood cells which are infected with the parasite P. falciparum cause the cells to become sticky and less deformable. This results in a build-up of cells on the vascular wall and creates occlusions to blood flow which are thought to cause the cerebral, renal and liver complications of P. falciparum infections. Certain esters of castanospermine prevent or reduce the adhesion of falciparum infected blood cells to the vascular endothelial wall and are a useful adjunct in the treatment of malaria.

Synthesis of potent anti-HIV agents: esters of castanospermine

The syntheses of 6-O- and 7-O-acyl-derivatives of the indolizidine alkaloid castanospermine, are described. These compounds are potent inhibitors of the human immunodeficiency virus (HIV) and are potential anti-AIDS agents.