124338-54-1

Upstream product

• 2747-38-8 methyltrichlorotitanium 
• 99032-03-8 (3S)-3-(Benzyloxy)butanal 
• 100-39-0 benzyl bromide 
• 42075-32-1 (2R,4R)-pentanediol 
• 1825-14-5 pentane-1,3-diol 
• 100-52-7 benzaldehyde 
• 86087-13-0 4,6-dimethyl-2-phenyl-(2α,4α,6β)-1,3-dioxane 

Downstream Products

• 2272-04-0 diphenyl[(4-carboxy)phenyl]phosphine oxide 
• 137626-31-4 (1'R,3'R)-1,1-bis<3'-(benzyloxy)-1'-methylbutoxy>heptane 
• 137626-38-1 (2R,4R)-2-(trimethylsiloxy)-4-(benzyloxy)pentane 

Relevant academic research and scientific papers

Stereoselective synthesis and reactions of secondary alkyllithium reagents functionalized at the 3-position

Secondary alkyllithium reagents bearing an OTBS group (TBS = tert-butyldimethylsilyl) at the 3-position can be prepared stereoconvergently through an I/Li exchange from a diastereomeric mixture of the corresponding secondary alkyl iodides. These lithium reagents react with a range of electrophiles, including carbon electrophiles, with retention of configuration to yield various 1,3-difunctionalized derivatives with good diastereoselectivities. Kinetic studies show that the 3- siloxy group strongly accelerates the epimerization at the lithium-substituted carbon atom. This method offers a new way to construct chiral open-chain molecules with excellent stereoselectivity.

A highly regio- and chemoselective reductive cleavage of benzylidene acetals with EtAlCl2-Et3SiH

A highly regio- and chemoselective reductive cleavage of benzylidene acetals derived from 1,2- and 1,3-diols was achieved under mild conditions using EtAlCl2-Et3SiH reagent system in good to excellent yields. Labile protecting groups

Mitsunobu reaction with 4-(diphenylphosphino)benzoic acid: A separation-friendly bifunctional reagent that serves as both a reductant and a pronucleophile

4-(Diphenylphosphino)benzoic acid was used for the Mitsunobu reaction as a bifunctional reagent that served as both a reductant and a pronucleophile. When combined with di-2-meth-oxyethyl azodicarboxylate, inversion of a secondary alcohol stereospecifically occurred to give an ester carrying a phosphine oxide group. The reaction mixture was directly hydrolyzed to give an inverted secondary alcohol in sufficient stereo and chemical purities by the presently developed chromatography-free process in conjunction with basic extraction, drying, and concentration. Georg Thieme Verlag Stuttgart - New York.

Optically active compound, liquid crystal composition containing said compound, and liquid crystal optical modulator using said composition

There are disclosed an optically active compound represented by the general formula: STR1 wherein n, R1, R2, R3, R4, Q1, Q2, Q3, and M are defined as in the detailed explanation,

Studies on the Mechanism and Origin of Stereoselective Opening of Chiral Dioxane Acetals

A systematic examination of the mechanism and origin of stereoselection in the reaction of dioxane acetals with allyltrimethylsilane was undertaken. Experimental tests for two limiting mechanisms, synchronous (SN-like) and dissociative (SN 1 -like) substitution processes, were investigated. The meso 2,4,6-trisubstituted 1,3-dioxane acetals cis- and trans-1 provided an interesting opportunity to test the timing of bond breaking and making in the substitution reaction. The modest and C(2)-substituent-dependent selectivity excluded the possibility of a direct SN2-type attack on a complexed acetal. Further, the enol ethers 3 and 5 and acyclic acetal 7 were studied as precursors of the putative oxocarbenium ion intermediate in the dissociative limit. The weak and inverted selectivity observed with these substrates ruled out the intermediacy of the extended, separated ion in reactions of the cyclic acetals under similar conditions. A unified mechanistic scheme involving three distinct ion pairs is proposed to explain the dependence of allylation selectivity on structural and experimental variables. The three species are analogous to those proposed in the classic Winstein scheme: (1) an intimate ion pair, (2) an external ion pair, and (3) a separated ion. Each of these proposed intermediates has a different stereochemical profile and the ultimate outcome is a composite of those factors that balance the contribution of the different intermediates. The influence of C(2) substituent, acetal configuration, Lewis acid type and stoichiometry, allylsilane stoichiometry, concentration, solvent, and temperature were investigated and integrated in the proposed mechanistic scheme.