16354-89-5

Basic information

• Product Name: (R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol
• Synonyms: (R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol
• CAS NO: 16354-89-5
• Molecular Weight: 208.257
• Mol File: 16354-89-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol(16354-89-5)
• EPA Substance Registry System: (R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol(16354-89-5)

Safety Data

• Hazardous Substances Data: 16354-89-5(Hazardous Substances Data)

Upstream product

• 100-58-3 phenylmagnesium bromide 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 591-51-5 phenyllithium 
• 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 
• 100-59-4 phenylmagnesium chloride 
• 16354-97-5 [(R)-2,2-dimethyl-1,3-dioxolan-4-yl]phenylmethanone 
• 108-86-1 bromobenzene 

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 
• 212574-38-4 Tributyl-{(R)-1-[(R)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenyl-methoxy]-propyl}-stannane 
• 13136-54-4 (R)-Benzyloxy-phenyl-acetic acid 
• 1239892-68-2 (2R,3R)-3-(benzyloxy)-3-phenylpropane-1,2-diol 

Relevant articles and documents

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.

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.

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