16354-89-5

Upstream product

• 100-58-3 phenylmagnesium bromide 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 591-51-5 phenyllithium 
• 100-59-4 phenylmagnesium chloride 
• 108-86-1 bromobenzene 
• 64870-23-1 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 102418-34-8 1,2:5,6-bis-O-(1-methylethylidene)-D-mannitol 
• 16354-97-5 [(R)-2,2-dimethyl-1,3-dioxolan-4-yl]phenylmethanone 

Downstream Products

• 87604-48-6 (R)-4-((R)-Benzyloxy-phenyl-methyl)-2,2-dimethyl-[1,3]dioxolane 
• 87604-47-5 (R)-4-((S)-Benzyloxy-phenyl-methyl)-2,2-dimethyl-[1,3]dioxolane 
• 164327-64-4 (2Z,6S,7R)-7,8-dihydroxy-5-oxa-6-phenyl-2-octenoic acid methyl ester 
• 164327-62-2 (2E,6S,7R)-7,8-dihydroxy-5-oxa-6-phenyl-2-octenoic acid methyl ester 
• 164327-54-2 (Z)-4-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-phenyl-methoxy]-but-2-enoic acid methyl ester 
• 164327-52-0 (E)-4-[(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-phenyl-methoxy]-but-2-enoic acid methyl ester 

Relevant academic research and scientific papers

Total Synthesis of the Putative Structure of Asperipin-2a and Stereochemical Reassignment

The total synthesis of the putative structure of asperipin-2a is described. The synthesis features ether cross-links between the phenolic oxygen of Tyr6 and the β position of Tyr3 and the phenolic oxygen of Tyr3 and the β position of Hpp1 in the unique 17- and 14-membered bicyclic structure of asperipin-2a, respectively. The synthesized putative structure does not match the natural product, and a stereochemical reassignment is postulated.

Preparation of chiral sugar-derived fluorides using new nucleophilic fluorinating reagents

New fluorinating reagents, composed of (S)-2-(diphenylmethyl)pyrrolidine and 1,1,3,3,3-pentafluoropropene/hexafluoropropene, have been found to be an effective system for nucleophilic deoxyfluorination. Regio- and stereoselectivity of deoxyfluorination of sugar-derived allylic, benzylic and propargylic alcohols with new reagents have been studied.

Further uses of pyrrole-based dienoxysilane synthons: A full aldol approach to azabicyclo[x.2.1]alkane systems

Two racemic 2-azabicyclo[2.2.1]heptane structures, 15 and 21, and two chiral non-racemic 6-azabicyclo[3.2.1]octane representatives, 28 and 36, have been synthesized starting from 1-(tert-butoxycarbonyl)-2-(tert- butyldimethylsilyloxy)-pyrrole (TBSOP, 5) and suitable ketones, 9, 16, 22 and 29. 2-Azabicycle 15 was then elaborated to racemic cyclopentane amino acid 38, while 6-azabicycle 36 served to access the enantiomerically pure normorphan-type structure 40. For all substrates, a uniform synthetic scheme was implemented based on the combination of two diastereoselective aldol-type carbon-carbon bond-forming reactions, the efficiencies of which were secured by appropriate aldol-stabilizing steps. A mechanistic rationale accounting for the markedly diastereoselective character of the key Mukaiyama aldol reactions between TBSOP and the ketone acceptors has been postulated that involves hetero-Diels-Alder transition-state structures in which the preference for endo versus exo addition is governed by the electronic nature of the substituents in the ketone substrates. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Comparison of Stereoselectivity of Intramolecular Cyclization of Aldehydes Tethered with Conjugated Esters Induced by O-Stannyl and O-Samarium Ketyls to Form the Tetrahydrofuran Ring Systems

Several (E)- and (Z)-ω-formyl-5-oxa-2-substituted-α,β-unsaturated esters (6Za-6Zc; 6Ea-6Ec; 6Eb'-6Ec'; 6Zb'-6Zc') were prepared in high yields.They were subjected to cyclization of their intramolecular ketyl radicals induced by either samarium(II) iodide

Stereoselectivity syn-Reduction of (R)-4-Acyl-2,2-dimethyl-1,3-dioxolanes with Metal Hydride Reagents

Lithium tri-s-butylborohydride and lithium aluminum hydride were found to be efficient reducing agents for the stereoselective preparation of syn-glycerol derivatives from (R)-4-acyl-2,2-dimethyl-1,3-dioxolanes.The scope and limitation of the stereoselect

Synthesis of the rarely obtained syn-Adducts in the Reaction of Organocopper Compounds with 2,3-O-Isopropylideneglyceraldehyde. Preparation of Optically Active Epoxy Alcohols

Organocopper compounds, prepared from Grignard reagents and copper(I) iodide in tetrahydrofuran-dimethyl sulphide, react with 2,3-O-isopropylideneglyceraldehyde highly stereoselectively (>10:1) affording the rarely obtained syn-addition products which can be readily converted into optically active epoxy alcohols, useful intermediates in organic synthesis.

ON THE STERIC COURSE OF THE ADDITION OF SOME ORGANOMETALLIC REAGENTS TO (R)-2,3-ISOPROPYLIDENE GLYCERALDEHYDE. SYNTHESIS OF OPTICALLY ACTIVE α-BENZYLOXY ALDEHYDES, ALCOHOLS, CARBOXYLIC ACIDS AND 1,2-DIOLS.

Organo-titanium and organo-zinc reagents were added stereoselectively to (R)-2,3-isopropylidene glyceraldehyde (1) to give the alcohols 2/3, which were converted into the optically active derivatives 4-11.