138662-21-2

Upstream product

• 39520-63-3 (Z)-5-phenylpent-2-en-1-ol 
• 75553-23-0 (E)-5-phenyl-2-penten-1-ol 
• 142528-79-8 cis S-tert-Butyl 3-(2-phenylethyl)oxirane-2-carbothioate 
• 142528-79-8 trans S-tert-Butyl 3-(2-phenylethyl)oxirane-2-carbothioate 

Downstream Products

• 99773-55-4 trans-2,3-epoxy-5-phenylpentanal 
• 99773-48-5 (2S,3S)-3-Phenethyl-oxirane-2-carboxylic acid 
• 92945-17-0 (2R,3S)-2-Methyl-5-phenyl-pentane-1,3-diol 
• 138560-10-8 Acetic acid (2R,3R)-2-acetylsulfanyl-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentyl ester 
• 138559-97-4 (R)-4-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-3-phenyl-propyl]-[1,3]oxathiolane-2-thione 
• 138560-42-6 Acetic acid (2R,3R)-2-acetylsulfanyl-3-hydroxy-5-phenyl-pentyl ester 
• 138560-09-5 (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-mercapto-5-phenyl-pentan-1-ol 

Relevant academic research and scientific papers

Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer

A simple and highly efficient synthetic route has been developed for synthesis of (R)-rugulactone (1a), (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6- dihydro-pyran-2-one (1b) and its 4S epimer 1c by employing proline-catalyzed α-aminooxylation, Sharpless epoxidation, Mitsunobu reaction as chirality introuducing steps. The antibacterial and antifungal activity of the compounds 1a, 1b and 1c were evaluated. 1a and 1b showed better antibacterial activity against Pseudomonas aeroginosa (MIC =12.5 μg/ml for 1a, 25 μg/ml for 1b) Klebsiella pneumonia (MIC =25 μg/ml for 1a). Compounds (1a, 1b, 1c) exhibited good to moderate antifungal activity.

Superbase-promoted rearrangement of oxiranes to cyclopropanes

Aryl- and alkenyl substituted oxiranes, when submitted to treatment with superbasic reagents, undergo a highly regio- and stereoselective rearrangement leading to cyclopropylmethanol derivatives. The process can also be applied to mono- and dihydroxy subs

Stereocontrol of the Horner-Wadsworth-Emmons Reaction: Application to the Synthesis of HIV-1 Protease Inhibitors

A systematic study on the Horner-Wadsworth-Emmons (HWE) reaction has shown that ethyl diphenylphosphonoacetate and methyl diphenylphosphonoacetate give a high excess of (Z)-alkenes. These reaction conditions were then used to prepare (Z)-ethyl-5-phenylpent-2-enoate, the corresponding (E)-isomer being prepared by standard Wittig chemistry. Reduction of each allylic ester, with diisobutylaluminium hydride (DIBAL), gave the allylic alcohols (15) and (19), respectively. Epoxidation of (15) and (19), under Sharpless conditions, gave separate samples of all four stereoisomers of 2,3-epoxy-5-phenylpentan-1-ol. Esterification of each isomer with Cbz-valine, under Mitsunobu conditions, provided (9)-(12) which were assayed against HIV protease. The cis series (9)-(10) proved to be significantly more potent than the trans (11)-12) and, within each of these series, the isomers derived from L-diisopropyltartrate [(9) and (11)] were the most active.

Simple cis-epoxide-based inhibitors of HIV-1 protease

The 4-nitrophenoxy-based epoxide 6a, conveniently synthesized using Sharpless epoxidation chemistry, has been shown to be an irreversible inhibitor of HIV-1 protease (k(inact) 1.8 μM, pH 6.5, I = 0.1 M). Related analogues, differing in the mode of attachm

Synthetic applications of glycidic thiolesters. Regioselective reduction to 1,3-diols and 2,3-epoxy alcohols

Glycidic thiolesters were shown to undergo regioselective reduction with Raney nickel to give 1,3-diols.With sodium borohydride at room temperature and lithium aluminum hydride at -78 deg C, the reduction of glycidic thiolesters was found to proceed chemo

Stereocontrolled Preparation of Cyclic Xanthate; a Novel Synthetic Route to 4-Thiofuranose and 4'-Thionucleoside

Optically active cyclic xanthate was prepared by the reaction of an epoxy alcohol with NaH and CS2, and was found to be a useful intermediate for synthesis of 4-thio-2-deoxyribose and 4'-thio-2'-deoxyribonucleoside.