172323-66-9

Usage

Uses

Used in Pharmaceutical Industry:
(2S)-3,6-dihydro-2H-pyran-2-ylmethanol is used as a building block in organic synthesis for the production of various pharmaceuticals and fine chemicals. Its stability and unique ring structure make it a valuable compound in the field of organic chemistry.
Used in Organic Synthesis:
(2S)-3,6-dihydro-2H-pyran-2-ylmethanol is used as a reagent in chemical reactions due to its stability and unique ring structure. It plays a crucial role in the synthesis of various organic compounds.

Upstream product

• 42757-04-0 ethyl 3,6-dihydro-2H-pyran-2-carboxylate 
• 445027-91-8 (2R)-N-[(1S)-3,6-dihydro-2H-pyran-2-ylmethanoyl]bornane-10,2-sultam 
• 924-53-8 isopropyl glyoxalate 
• 106-99-0 buta-1,3-diene 

Downstream Products

• 170277-79-9 (3S)-3-(2-hydroxyethoxy)-4-(triphenylmethoxy)-1-butanol 
• 170277-77-7 (S)-3-[2-{(methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol methanesulfonate 
• 602326-63-6 (S)-2-(benzyloxymethyl)-3,6-dihydro-2H-pyran 
• 124662-66-4 (6S)-6-[(phenylmethoxy)methyl]-5,6-dihydro-2H-pyran-2-one 
• 94480-29-2 (2S)-2-benzyloxymethyl-2,3-dihydro-4H-pyran-4-one 
• 885666-75-1 (6S)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-one 
• 364730-56-3 (S)-2-trityloxymethyl-3,6-dihydro-2H-pyran 

Relevant academic research and scientific papers

Diastereoselective Reaction of Buta-1,3-diene with Chiral Derivatives of Glyoxylic Acid: Effective Route to Optically Pure 2-Substituted 3,6-Dihydro2H-pyrans

The influence of Lewis acids on the diastereoselectivity of [4+2] cycloaddition of buta-1,3-diene (4) to N-glyoxyloyl-(2R)-bornane- 10,2-sultam (6a) and (R)-8-phenylmenthyl glyoxylate (6b) was investigated and found to have high levels of asymmetric induc

Asymmetric Hetero Diels-Alder Reactions and Ene Reactions Catalyzed by Chiral Copper(II) Complexes

A new copper(II) bisoxazoline-catalyzed reaction of glyoxylate esters with dienes leading to the hetero Diels-Alder product and the ene product in high yield and with a high enantiomeric excess (ee) has been developed.The hetero Diels-Alder product:ene product ratio is in the range 1:0.6 to 1:1.8 and is dependent on both the chiral ligand attached to the metal, the glyoxylate ester, and the reaction temperature.The scope of the copper(II) bisoxazoline-catalyzed reaction of glyoxylate esters with dienes is demonstrated by the reaction of a variety of different dienes with ethyl and isopropyl glyoxylate, and it is shown that a simple substrate such as 1,3-butadiene reacts to give the hetero Diels-Alder product in 55percent yield with an ee 87percent.Furthermore, the synthetic application of the reaction is demonstrated by the synthesis of a highly interesting synthon for sesquiterpene lactones in high yield and diastereoselectivity, and with a very high ee from 1,3-cyclohexadiene and ethyl glyoxylate using a copper(II) bisoxazoline as the catalyst.A mechanism for the hetero Diels-Alder reaction, which accounts for the enantioselectivity in the reactions, is proposed.

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.