364730-56-3

Usage

Uses

Used in Organic Synthesis:
(2S)-2-[(trityloxy)methyl]-3,6-dihydro-2H-pyran is used as a building block in organic synthesis for the creation of various complex organic molecules. Its trityloxy group provides a temporary protective function for alcohols, facilitating the synthesis process and allowing for selective reactions to occur.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (2S)-2-[(trityloxy)methyl]-3,6-dihydro-2H-pyran is employed as a key intermediate in the synthesis of natural products and pharmaceuticals. Its unique structure and reactivity contribute to the development of new compounds with potential therapeutic applications.
Used in Protecting Group Chemistry:
The trityloxy group in (2S)-2-[(trityloxy)methyl]-3,6-dihydro-2H-pyran is used as a protecting group for alcohols in protecting group chemistry. This allows chemists to carry out reactions on other functional groups in a molecule without affecting the alcohol, which can then be selectively deprotected under acidic conditions when needed.

Upstream product

• 170277-78-8 1,1',1''-[[[(2S)-4-methyl-2-(2-propen-1-yloxy)-4-penten-1-yl]-oxy]methylidyne]trisbenzene 
• 42757-04-0 ethyl 3,6-dihydro-2H-pyran-2-carboxylate 
• 129940-50-7 (S)-tritylglycidol 
• 445027-91-8 (2R)-N-[(1S)-3,6-dihydro-2H-pyran-2-ylmethanoyl]bornane-10,2-sultam 
• 170277-82-4 (2S)-1-triphenylmethoxy-4-pentene-2-ol 
• 76-83-5 trityl chloride 
• 172323-66-9 (S)-(-)-(3,6-Dihydro-2H-pyran-2-yl)methanol 

Downstream Products

• 602326-67-0 1,5-anhydro-3-azido-3,4-dideoxy-5-O-trityl-D-arabino-hexitol 
• 602326-65-8 (2S,4R,5R)-4,5-epoxy-2-trityloxymethyl-tetrahydropyran 
• 602326-64-7 (2S,4S,5S)-4,5-epoxy-2-trityloxymethyl-tetrahydropyran 
• 170277-79-9 (3S)-3-(2-hydroxyethoxy)-4-(triphenylmethoxy)-1-butanol 

Relevant academic research and scientific papers

Synthesis of amino-1,4-anhydro-D-pentitols and amino-1,5-anhydro-D-hexitols with the arabino configuration from (R)-glycidol

2-Amino-1,4-anhydro-pentitol and 3-amino-1,5-anhydro-4-deoxy-hexitol with the arabino configuration were synthesised from (R)-glycidol using a metathesis reaction as the key step. The dihydrofuran or dihydropyran products obtained after the metathesis rea

Highly diastereoselective hetero-Diels-Alder reaction of buta-1,3-diene with N-glyoxyloyl-(2R)-bornane-10,2-sultam: An efficient synthesis of homochiral (S)-3-[2-{(methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol methanesulfonate

The influence of Lewis acid on the diastereoselectivity of [4+2] cycloaddition of buta-1,3-diene to N-glyoxyloyl-(2R)-bornane-10,2-sultam was investigated and high levels of asymmetric induction were achieved. (S)-3-[2-{(Methylsulfonyl)oxy}ethoxy]-4-(trip

Hetero Diels - Alder-biocatalysis approach for the synthesis of (S)-3-[2-{(methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol methanesulfonate, a key intermediate for the synthesis of the PKC inhibitor LY333531

A cost-effective and easily scaled-up process has been developed for the synthesis of (S)-3-[2-{(methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol methanesulfonate, a key intermediate used in the synthesis of a protein kinase C inhibitor drug through a combination of hetero Diels - Alder and biocatalytic reactions. The Diels - Alder reaction between ethyl glyoxylate and bntadiene was used to make racemic 2-ethoxy-carbonyl-3,6-dihydro-2H-pyran. Treatment of the racemic ester with Bacillus lentus protease resulted in the selective hydrolysis of the R-enantiomer and yielded S-2-ethoxycarbonyl-3,6-dihydro-2H-pyran in excellent optical purity, which was reduced to S-3,6-dihdro-2H-pyran-2-yl methanol. Tritylation of this alcohol, followed by reductive ozonolysis and mesylation afforded the product in 10-15% overall yield and with >99% ee and chemical purity. Details of the process development work done on each step are given.