16354-91-9

Basic information

• Product Name: (S)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol
• Synonyms: (S)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol
• CAS NO: 16354-91-9
• Molecular Weight: 208.257
• Mol File: 16354-91-9.mol

Chemical Properties

• CAS DataBase Reference: (S)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol(16354-91-9)
• EPA Substance Registry System: (S)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol(16354-91-9)

Safety Data

• Hazardous Substances Data: 16354-91-9(Hazardous Substances Data)

Upstream product

• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 591-51-5 phenyllithium 
• 102418-34-8 1,2:5,6-bis-O-(1-methylethylidene)-D-mannitol 
• 100-58-3 phenylmagnesium bromide 
• 108-86-1 bromobenzene 
• 100-59-4 phenylmagnesium chloride 
• 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 
• 16354-95-3 (1S,2R)-1-phenylpropane-1,2,3-triol 
• 164327-42-8 (R)-4-((S)-Allyloxy-phenyl-methyl)-2,2-dimethyl-[1,3]dioxolane 
• 164327-57-5 (2Z,6R,7R)-7,8-dihydroxy-5-oxa-6-phenyl-2-octenoic acid methyl ester 
• 164327-60-0 (2E,6R,7R)-7,8-dihydroxy-5-oxa-6-phenyl-2-octenoic acid methyl ester 
• 164327-47-3 (Z)-4-[(S)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-phenyl-methoxy]-but-2-enoic acid methyl ester 
• 164327-50-8 (E)-4-[(S)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-phenyl-methoxy]-but-2-enoic acid methyl ester 
• 201420-76-0 [(S)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-phenyl-methoxy]-acetic acid ethyl ester 
• 212574-39-5 Tributyl-{(R)-1-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenyl-methoxy]-propyl}-stannane 

Relevant articles and documents

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

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.