111902-61-5

Upstream product

• 42134-55-4 (E)-3-cyclohexyl-2-propen-1-ol 
• 1195778-34-7 C₁₇H₂₉NO₃S 
• 42134-55-4 3-cyclohexyl-2-propen-1-ol 
• 142528-81-2 cis S-tert-Butyl 3-cyclohexyloxirane-2-carbothioate 
• 1438398-80-1 C₁₆H₂₇NO₃S 
• 1285721-42-7 C₂₃H₃₃NO₄S 
• 1285721-23-4 C₁₈H₃₁NO₃S 
• 2043-61-0 cyclohexanecarbaldehyde 
• 4484-35-9 3-cyclohexylacrylic acid 
• 705-95-3 3-cyclohexylacrylic acid methyl ester 

Downstream Products

• 172376-40-8 (S)-1-cyclohexyl-1,3-propanediol 
• 216088-17-4 (S)-3-cyclohexyl-1,2-propanediol 
• 1195780-45-0 C₁₉H₂₃F₃O₄ 
• 475056-70-3 (2S,3R)-3-cyclohexyloxirane-2-carbaldehyde 
• 80542-17-2 (2R,3S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-3-hydroxypropanoic acid 
• 1280013-67-3 (2S,3S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-3-hydroxypropanoic acid 
• 1280013-68-4 C₂₆H₃₉N₃O₃ 
• 1280013-70-8 C₂₆H₃₉N₃O₃ 
• 1280013-74-2 C₁₉H₃₃N₃O₃ 
• 674782-28-6 C₃₃H₄₃N₃O₆ 
• 674782-28-6 C₃₃H₄₃N₃O₆ 
• 499783-91-4 [(2S,3R)-3-cyclohexyloxiran-2-yl]carboxylic acid 
• 80542-16-1 D-threo-2-amino-3-cyclohexyl-3-hydroxypropionic acid 
• 461023-63-2 4-[4-(((3R)-1-butyl-3-[(S)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl)methyl)phenoxy]benzoic acid hydrochloride 

Relevant academic research and scientific papers

New one-pot procedure for the synthesis of diprotected amino alcohols from unprotected vinyl aziridines

An unprecedented one-pot reaction that allows the synthesis of diprotected amino alcohols from unprotected vinyl aziridines is reported. The results demonstrate the possibility to use various acyl chlorides in order to obtain differently functionalised fragments. Mechanistic insights are given.

A highly stereoselective synthesis of glycidic amides based on a new class of chiral sulfonium salts: Applications in asymmetric synthesis

A new type of chiral sulfonium salts that are characterized by a bicyclic system has been designed and synthesized from α-amino acids. Their corresponding ylides, which were prepared by basic treatment of the sulfonium salts, reacted smoothly with a broad array of simple and chiral aldehydes to provide trans-epoxy amides in reasonable to very good yields and excellent stereoselectivities (>98 %). The obtained epoxy amides were found to be useful as synthetic building blocks. Thus, they were reduced into their corresponding epoxy alcohols and subjected to oxirane-ring-opening reactions with different types of nucleophiles.

A highly regioselective azidolysis of 2,3-epoxy amines: An unexpected [Ti(O-i-Pr)2(N3)2] mediated C-2 opening

The Lewis acid-catalysed regioselective azidolysis of 2,3-epoxy amines has been investigated. The results obtained demonstrated that using TMSN3 as a source of azide, the appropriate choice of Lewis acid allowed to direct the regiochemistry of the ring opening. The present methodologies provide a powerful tool in organic synthesis for the preparation of diaminoalcohol moieties.

Cyclic sulfur ylides derived from gleason-type chiral auxiliaries for the asymmetric synthesis of epoxy amides

Gleason-type chiral auxiliaries were used for the synthesis of a novel class of sulfonium salts, obtained via methylation of the sulfide with Meerwein's salt. The salts were reacted with aldehydes under basic conditions to provide epoxy amides, which were reduced to their corresponding epoxy alcohols in excellent enantiomeric excesses. Interestingly, it was feasible to synthesize both enantiomeric epoxy alcohols depending on which of the sulfonium salts, prepared from L-amino acids (6 and 9 from L-valine or 15 and 16 from L-serine) was employed.

Spirodiketopiperazine-based CCR5 antagonist: Discovery of an antiretroviral drug candidate

Following the discovery that hydroxylated derivative 3 (Fig. 1) was one of the oxidative metabolites of the original lead 1, it was found that hydroxylated compound 4 possesses higher in vitro anti-HIV potency than the corresponding non-hydroxylated compo

Discovery of 4-[4-({(3R)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5- dioxo-1,4,9-triazaspiro[5.5]undec-9-yl}methyl)phenoxy]benzoic acid hydrochloride: A highly potent orally available CCR5 selective antagonist

Based on the original spirodiketopiperazine design framework, further optimization of an orally available CCR5 antagonist was undertaken. Structural hybridization of the hydroxylated analog 4 derived from one of the oxidative metabolites and the new orally available non-hydroxylated benzoic acid analog 5 resulted in another potent orally available CCR5 antagonist 6a as a clinical candidate. Full details of a structure-activity relationship (SAR) study and ADME properties are presented.

A highly efficient methodology of asymmetric epoxidation based on a novel chiral sulfur ylide

A new type of chiral sulfur ylides has been synthesized and their reactivities against carbonyl compounds tested, showing a high degree of stereoselectivity in the formation of trans epoxy amides under very mild reaction conditions.

Prompt determination of absolute configuration for epoxy alcohols via exciton chirality protocol

A microscale protocol for determination of absolute configurations of 2,3-epoxy alcohols is described. 2,3-Disubstituted (cis and trans), 2,2-disubstituted, 2,2,3-trisubstituted, and 2,3,3-trisubstituted epoxy alcohols rendered prominent ECCD signals upon complexing with a Lewis acidic porphyrin tweezer and consequently provide straightforward assignment of chirality for epoxy alcohols. This method proved to be rapid, simple, sensitive, and reliable for the class of molecules listed above. Copyright

The silylalkyne-prins cyclization: Stereoselective synthesis of tetra- and pentasubstituted halodihydropyrans

A new type of Prins cyclization using silylated secondary homopropargylic alcohols and aldehydes yielding tetra- and pentasubstituted dihydropyrans is described. The presence of the trimethylsilyl group in the triple bond favors the Prins cyclization and

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