4105-60-6

Usage

Uses

Used in Fragrance Industry:
2,2-DIMETHYL-5-VINYL-[1,3]DIOXOLANE-4-CARBALDEHYDE is used as a fragrance ingredient for its sweet, floral scent, adding pleasant aromas to various consumer products.
Used in Flavor Industry:
In the flavor industry, 2,2-DIMETHYL-5-VINYL-[1,3]DIOXOLANE-4-CARBALDEHYDE serves as a flavoring agent, enhancing the taste of food products by imparting a sweet, floral flavor profile.
Used in Pharmaceutical Industry:
2,2-DIMETHYL-5-VINYL-[1,3]DIOXOLANE-4-CARBALDEHYDE is utilized in the production of pharmaceuticals, potentially contributing to the development of new drugs or improving the efficacy of existing ones.
Used in Food Products:
2,2-DIMETHYL-5-VINYL-[1,3]DIOXOLANE-4-CARBALDEHYDE is used as a flavoring agent in food products, providing a sweet, floral taste that can enhance the overall flavor experience.
Used in Cosmetics and Personal Care Products:
In cosmetics and personal care products, 2,2-DIMETHYL-5-VINYL-[1,3]DIOXOLANE-4-CARBALDEHYDE is used as a fragrance, adding a pleasant scent to these products and improving the sensory experience for consumers.
Used in Preservation of Consumer Products:
2,2-DIMETHYL-5-VINYL-[1,3]DIOXOLANE-4-CARBALDEHYDE's antimicrobial properties make it useful in the preservation of various consumer products, helping to prevent the growth of microorganisms and extend the shelf life of products.
It is important to handle 2,2-DIMETHYL-5-VINYL-[1,3]DIOXOLANE-4-CARBALDEHYDE with care, as it may cause irritation to the skin, eyes, and respiratory system. Proper safety measures should be taken during its use in different applications.

InChI:InChI=1/C8H12O3/c1-4-6-7(5-9)11-8(2,3)10-6/h4-7H,1H2,2-3H3/t6-,7+/m0/s1

Upstream product

• 67-56-1 methanol 
• 155934-55-7 (4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde 
• 139326-94-6 1,2:3,4-di-O-isopropylidene-5,6-di-O-mesyl-D-mannitol 
• 4239-90-1 (4S,4'R,5R)-2,2,2',2'-tetramethyl-5-vinyl-4,4'-bi(1,3-dioxolane) 
• 188567-96-6 (3R,4R)-5-(tert-butyldimethylsiloxy)-3,4-(isopropylidenedioxy)pent-1-ene 
• 125993-65-9 (4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 
• 168109-89-5 (1R)-1-((4R,5R)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)ethane-1,2-diol 
• 114817-96-8 [(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methanol 

Downstream Products

• 476153-89-6 (R)-((4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)(phenyl)methanol 
• 476153-90-9 (S)-((4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)(phenyl)methanol 
• 188568-03-8 (4R,5R)-4-((R)-2-Iodo-4-isopropenyl-cyclohex-1-enylmethyl)-2,2-dimethyl-5-vinyl-[1,3]dioxolane 
• 18178-54-6 (-)-rishitin 
• 476153-94-3 (1S,5S,7S,8R)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one 
• 476153-93-2 (1S,5S,7R,8R)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one 
• 476153-91-0 (1R,2S,3R)-1-phenyl-pent-4-ene-1,2,3-triol 
• 476153-92-1 (1S,2S,3R)-1-phenyl-pent-4-ene-1,2,3-triol 
• 870093-68-8 (2R,3R)-3-[(4R,5R)-2,2-Dimethyl-5-((E)-styryl)-[1,3]dioxolan-4-yl]-3-hydroxy-2-methoxy-N-((S)-2-oxo-azepan-3-yl)-propionamide 
• 921763-52-2 (4R,5R)-4-((E)-4-{(2S,4S,5R)-4-(dimethyl-phenyl-silanyl)-5-[(1S,2R,3R)-2-(4-methoxybenzyloxy)-3-methyl-1-triethylsilanyloxy-hex-5-ynyl]-tetrahydro-furan-2-yl}-but-1-enyl)-2,2-dimethyl-5-vinyl-[1,3]dioxolane 
• 921763-76-0 [(1R,2R,3R)-1-{(2S,5S)-5-[(E)-4-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyl]-tetrahydro-furan-2-yl}-2-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyloxy]-triethyl-silane 
• 921763-75-9 (1R,2R,3R)-1-{(2S,5S)-5-[(E)-4-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyl]-tetrahydro-furan-2-yl}-2-(4-methoxy-benzyloxy)-3-methyl-hex-5-yn-1-ol 

Relevant academic research and scientific papers

Total synthesis of marine natural products separacenes A and B

A short and convergent route for the stereoselective total synthesis of separacenes A and B has been developed using (+)-methyl d-lactate and d-(-)-tartaric acid as the chiral pools. The characteristic features of this synthesis include the Trost-Rychnovsky alkyne rearrangement to construct the C7-C9 conjugated diene, the Horner-Wadsworth-Emmons olefination to form the C5-C6 and C11-C12 olefins and the Corey-Bakshi-Shibata reaction to install the C-13 hydroxy functionality.

Chiron approach for the total synthesis of (+)-synargentolide B

A concise and efficient chiron approach for the total synthesis of natural product synargentolide B was achieved in 10 steps with overall yields of 11.3% from D-mannitol and L-ethyl lactate. The key reactions included anti-Barbier allylation, cross-metathesis, and an intramolecular Yamaguchi esterification.

Tandem ring-closing/cross-metathesis approach for the synthesis of synargentolide B and its stereoisomers

The stereoselective syntheses of synargentolide B and its three stereoisomers have been accomplished from L-(+)- and D-(-)-diethyl tartrates, D-ribose, and D-mannitol as chiral pool starting materials. The key step was a tandem ring-closing/cross-metathes

Epi -, Epoxy-, and C2-modified bengamides: Synthesis and biological evaluation

With the objective of investigating the influence of structural modifications of the polyketide chain of the bengamides upon their antitumoral activities, we targeted the preparation of bengamide E analogues with modification of the stereochemistry at C-2 and at C-3, the substituent at the C-2 position, and the presence of oxirane rings. For the synthesis of these analogues, a new synthetic method for asymmetric epoxidation, developed in our laboratories, was employed utilizing the chiral sulfonium salts 22 and 23. In order to access 2-epi-bengamide E from these epoxy amides, a synthetic methodology, developed by Miyashita, allowed an oxirane-ring-opening reaction with a double inversion of the configuration. Alternatively, an aldol reaction provided access to the same analogue in a shorter and more efficient manner. Finally, biological evaluation of all of these bengamide E analogues demonstrated that the polyketide chain is essential for the antitumor activity of these natural products, not being amenable to structural or configurational modifications.

Stereoselective and facile total synthesis of (+)-goniodiol, a styryllactone from carbohydrates

The stereoselective synthesis of (+)-goniodiol, a cytotoxic styryllactone, has been accomplished in 10 steps starting from inexpensive and readily available d-manitol and δ-gluconolactone involving the direct and straightforward reaction conditions of Gri

Doubly diastereoselective conjugate addition of homochiral lithium amides to homochiral α,β-unsaturated esters containing cis- and trans-dioxolane units

As part of a long-term goal directed towards the ab initio asymmetric synthesis of unnatural amino sugars, the doubly diastereoselective conjugate addition reactions of the antipodes of lithium N-benzyl-N-(α-methylbenzyl) amide to a range of homochiral α,β-unsaturated esters containing cis- and trans-dioxolane units was investigated. These reactions resulted in "matching" and "mismatching" effects. In the "matched" cases a single diastereoisomer of the corresponding β-amino ester (containing three contiguous stereocentres) is produced. Upon conjugate addition to a homochiral α,β-unsaturated ester containing a cis-dioxolane unit, in the "mismatched" case it is the stereocontrol of the substrate which is dominant over that of the lithium amide, whilst upon addition to homochiral α,β-unsaturated esters containing a trans-dioxolane unit the stereocontrol of the homochiral lithium amide is dominant. Hydrogenolytic N-deprotection of the β-amino ester products of conjugate addition gives access to polyoxygenated β-amino acid derivatives.

Total syntheses of (+)-7-epi-goniofufurone, (+)-goniopypyrone and (+)-goniofufurone from a common precursor

Total syntheses of (+)-7-epi-goniofufurone, (+)-goniopypyrone and (+)-goniofufurone have been achieved from an advanced common precursor formed from d-(+)-mannitol by changing the carbinol protection profile. The Royal Society of Chemistry.

Total synthesis of amphidinolide E and amphidinolide E stereoisomers

Four amphidinolide E stereoisomers, amphidinolide E (1), 2-epi-amphidinolide E (2), 19-epi-amphidinolide E (3), and 2-epi-19-epi-amphidinolide E (4), have been synthesized via the judicious union of aldehyde 5, allylsilanes 7 or 8, acids 9 or 10, and viny

Total synthesis of amphidinolide E

A convergent and highly stereocontrolled synthesis of amphidinolide E (1) has been accomplished. The synthesis features a highly diastereoselective (>20:1) BF3·Et2O promoted [3+2] annulation reaction between aldehyde 3 and allylsilan

Synthesis of (+)-goniothalesdiol and (+)-7-epi-goniothalesdiol

A total synthesis of (+)-goniothalesdiol, a 3,4-dihydroxy-2,5-disubstituted tetrahydrofuran isolated from Goniothalamus borneensis (Annonaceae), and its 7-epimer is reported using oxycarbonylation methodology for construction of polyhydroxylated substitut