189328-24-3

Usage

Explanation

The compound is composed of 23 carbon atoms, 24 hydrogen atoms, and 5 oxygen atoms.

Explanation

The compound features a spiro[4.4]nonane ring system, which is a fused ring system consisting of two nonane rings connected at a single carbon atom, and a ketone functional group (C=O) present in the molecule.

Explanation

The compound exists in three different stereoisomeric forms, which are variations of the molecule with the same molecular formula but different spatial arrangements of the atoms.

Explanation

The (3R,4S,5R)isomer is one of the three stereoisomeric forms of the compound, characterized by the specific arrangement of the phenylmethoxy groups at the 3rd, 4th, and 5th carbon atoms of the spiro[4.4]nonane ring system.

Explanation

The compound has two phenylmethoxy groups (C6H5-O-CH3) attached to the 3rd and 4th carbon atoms of the spiro[4.4]nonane ring system, which contribute to its unique properties.

Explanation

As a complex organic molecule, it is expected that the compound would be soluble in common organic solvents such as dichloromethane, ethyl acetate, or acetone.

Explanation

The compound is likely stable under normal conditions, such as room temperature and atmospheric pressure, without undergoing significant decomposition or reaction.

Explanation

The melting point of the compound is not provided in the material, but it is an important physical property that can be determined experimentally.

Explanation

The boiling point of the compound is not provided in the material, but it is another important physical property that can be determined experimentally.

Chemical Structure

Spiroketone with a spiro[4.4]nonane ring system and a ketone functional group

Stereoisomerism

Three stereoisomeric forms

Specific Isomer

(3R,4S,5R)-

Phenylmethoxy Substituents

Two phenylmethoxy groups attached to the 3rd and 4th carbon atoms

Potential Applications

Organic synthesis and pharmaceuticals

Solubility

Likely soluble in organic solvents

Stability

Stable under normal conditions

Melting Point

Unknown (specific value not provided)

Boiling Point

Unknown (specific value not provided)

Upstream product

• 100-39-0 benzyl bromide 
• 1353888-95-5 3,4-bis(benzyloxy)-6-hydroxy-1,7-dioxaspiro[4.4]nonan-8-one 
• 1353888-63-7 methyl 4,5-bis(benzyloxy)-2-oxabicyclo[4.1.0]heptane-7-carboxylate 
• 115220-82-1 (3R,4R)-3,4-Bis-benzyloxy-3,4-dihydro-2H-pyran 
• 1198472-39-7 C₂₁H₂₂N₂O₅ 
• 189328-23-2 ((2R,3S,4R)-3,4-Bis-benzyloxy-2-phenylethynyl-tetrahydro-furan-2-yl)-thioacetic acid S-tert-butyl ester 
• 189328-22-1 (3S,4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-phenylethynyl-hexanethioic acid S-tert-butyl ester 
• 197219-77-5 (3S,4S,5R)-4,5-Bis-benzyloxy-3,6-dihydroxy-3-phenylethynyl-hexanethioic acid S-tert-butyl ester 
• 197219-86-6 [(2R,3S,4R)-3,4-Bis-benzyloxy-2-((Z)-styryl)-tetrahydro-furan-2-yl]-thioacetic acid S-tert-butyl ester 
• 189328-21-0 (4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hex-1-yn-3-one 
• 197219-76-4 (4R,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hex-1-yn-3-ol 
• 171622-74-5 (2R,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol 
• 1055030-35-7 1-(tert-butyl-diphenyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxymethyl)-hept-6-ene-2,3,4-triol 
• 551-84-8 xylulose 

Relevant academic research and scientific papers

A concise and efficient approach to the stereoselective total synthesis of (+)-secosyrin 1 and (+)-syributin 1

A concise and stereoselective approach for the total synthesis of (+)-secosyrin 1 and (+)-syributin 1, metabolites of Pseudomonas syringae, is reported. The key synthetic step in this approach is a highly stereoselective construction of spiro center, through a one-pot dehydrohalogenation, intramolecular hetero-Michael addition (IHMA) and ester hydrolysis of halohydrins derived by the ring opening of 1,2-cyclopropanecarboxylated xylal derivative.

Stereoselective synthesis of sugar fused β-disubstituted γ-butyro-lactones: C-spiro-glycosides from 1,2-cyclopropanecarboxylated sugars

A stereoselective methodology was developed for the construction of C-spiro-glycosides in two steps involving bromonium ion activated solvolytic ring opening of sugar derived 1,2-cyclopropanecarboxylates followed by a one-pot dehydrohalogenation, intramolecular hetero-Michael addition (IHMA) and ester hydrolysis. The obtained spirocyclic lactols were further converted to enantiomerically pure spirolactones.

Spirolactone syntheses through a rhodium-catalyzed intramolecular C-H insertion reaction: Model studies towards the synthesis of syringolides

Model studies towards the total synthesis of syringolides using a rhodium-catalyzed intramolecular C-H insertion reaction as the key step are described. A highly stereospecific synthesis of spirolactones is achieved employing this methodology.

A formal synthesis of the syributins and secosyrins and a synthetic approach toward the syringolides

The indium-mediated allylation of a protected derivative of D-xylulose in aqueous THF is highly diastereoselective. The obtained product has been converted in four steps into a spiro lactone previously transformed into syributins and secosyrins. This remarkably short reaction sequence constitutes therefore a formal synthesis of these compounds and provides also a promising synthetic approach towards the syringolides.

First total synthesis of (+)-secosyrin 1

The first total synthesis of (+)-secosyrin 1, isolated from P. syringae, pv. tomato, was accomplished in a stereoselective manner from diisopropyl D-tartrate. This synthesis unambiguously established the stereochemistry of (+)-secosyrin 1.