The Synthetic Routes of 3-[(2S,5S)-5-[(3R,5R)-3-hydroxy-6-iodo-5-methylhept-6-enyl]-4-methylideneoxolan-2-yl]propyl 2,2-dimethylpropanoate

Synthetic routes of 3-[(2S,5S)-5-[(3R,5R)-3-hydroxy-6-iodo-5-methylhept-6-enyl]-4-methylideneoxolan-2-yl]propyl 2,2-dimethylpropanoate: A Comprehensive Review

3-[(2S,5S)-5-[(3R,5R)-3-hydroxy-6-iodo-5-methylhept-6-enyl]-4-methylideneoxolan-2-yl]propyl 2,2-dimethylpropanoate is an important compound in the field of organic synthesis, with potential applications in pharmaceuticals, agrochemicals, and other areas.
The synthesis of this compound involves multiple steps, and the choice of synthetic route depends on a variety of factors, including the availability of starting materials, the desired yield and purity of the product, and the cost and time required for the synthesis.
In this article, we will review some of the most common synthetic routes to 3-[(2S,5S)-5-[(3R,5R)-3-hydroxy-6-iodo-5-methylhept-6-enyl]-4-methylideneoxolan-2-yl]propyl 2,2-dimethylpropanoate, with a focus on the advantages and limitations of each route.

One of the most commonly used synthetic routes to 3-[(2S,5S)-5-[(3R,5R)-3-hydroxy-6-iodo-5-methylhept-6-enyl]-4-methylideneoxolan-2-yl]propyl 2,2-dimethylpropanoate is the Widmer-Roffino synthesis, which involves the condensation of 2,2-dimethylpropionic acid with 3-bromo-5-methylhept-6-enal in the presence of a Lewis acid catalyst, followed by reduction of the resulting β-ketone to an alcohol using a reducing agent such as lithium aluminum hydride (LiAlH4).
This route offers a good yield of the desired product, but requires the handling of hazardous reagents such as lithium and a Lewis acid catalyst, and can be expensive due to the cost of the reducing agent.

An alternative synthetic route to 3-[(2S,5S)-5-[(3R,5R)-3-hydroxy-6-iodo-5-methylhept-6-enyl]-4-methylideneoxolan-2-yl]propyl 2,2-dimethylpropanoate is the one-pot synthesis, which involves the condensation of 2,2-dimethylpropionic acid with 3-iodo-6-methylhept-5-enal in the presence of a base, such as sodium hydride (NaH), followed by reduction of the resulting α-chloroketone to an alcohol using a reducing agent such as hydride (H2) in the presence of a noble metal catalyst, such as platinum (Pt).
This route offers the advantage of a simple and efficient synthesis, but may require the use of expensive reagents such as NaH and Pt, and can be difficult to scale up.

Another synthetic route to 3-[(2S,5S)-5-[(3R,5R)-3-hydroxy-6-iodo-5-methylhept-6-enyl]-4-methylideneoxolan-2-yl]propyl 2,2-dimethylpropanoate is the one-pot cyclocondensation, which involves the condensation of 2,2-dimethylpropionic acid with 3-iodo-6-methylhept-5-enal in the presence of a base and a condensation catalyst, such as hydrochloric acid (HCl) or sulfuric acid (H2SO4), followed by reduction of the resulting α-chloroketone to an alcohol using a reducing agent such as lithium aluminum hydride (LiAlH4).