64031-36-3

Usage

Class

Dioxolane group (organic compounds with a five-membered ring and two oxygen atoms)

Uses

Production of pharmaceuticals
Solvent
Reagent in organic synthesis

Physical state

Colorless liquid

Odor

Slightly sweet, ether-like

Toxicity

Low toxicity, no significant health hazards associated with its use

Safety precautions

Proper handling and storage procedures should be followed to prevent exposure and accidents

Upstream product

• 69821-02-9 (R)-(+)-2,2,4-trimethyl-1,3-dioxolane-4-carboxaldehyde 
• 1138677-77-6 (R)-N-methoxy-N-methyl-2,2,4-trimethyl-1,3-dioxolane-4-carboxamide 
• 81600-36-4 (+/-)-2,2,4-trimethyl-1,3-dioxolane-4-carboxaldehyde 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 

Relevant academic research and scientific papers

A new tactic for tocopherol synthesis using intramolecular benzyne trapping by an alcohol

A formal total synthesis of (S)-α-Tocopherol, the major component of natural Vitamin E has been achieved using intramolecular benzyne trapping as a key step to form the chroman ring. The synthesis also features an efficient new method for benzotriazole N-Amination using an oxaziridine; chiral, nonracemic intermediates are generated using asymmetric dihydroxylation.

Enantioselective Total Syntheses of (R)- A nd (S)-Naphthotectone, and Stereochemical Assignment of the Natural Product

Both isomers of naphthotectone, an isoprenoid quinone from Verbenaceae Tectona grandis possessing interesting biological activities, were enantioselectively obtained by two different synthetic routes in which the carbon side-chain of the naphthoquinone core was introduced using either a Sonogashira or a Heck coupling reaction. In both cases, the naphthoquinone core of the final products was obtained by a late-stage anodic treatment. (R)-Naphthotectone was obtained in six steps from leuconaphthazarin with an overall yield of 38 % and an enantiomeric excess of 86 %. This compound was found to have the same absolute configuration as the natural product at its C-3′ stereogenic center. (S)-Naphthotectone was obtained in five steps from leuconaphthazarin with an overall yield of 36 % and an enantiomeric excess of 80 %. Naphthotectone was synthesized in both racemic and enantioenriched forms by two different synthetic strategies using Pd coupling reactions and anodic treatment as key steps. The stereochemistry of the natural product has been assigned.