69010-01-1

Upstream product

• 68972-93-0 (E)-1,4-bis(benzyloxy)-2-butene 
• 298-18-0 (S,S)-diepoxybutane 
• 100-51-6 benzyl alcohol 
• 68972-96-3 (Z)-1,4-dibenzyloxy-2-butene 
• 71806-86-5 (4R,5S)-4,5-bis((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolane 
• 100-39-0 benzyl bromide 
• 93877-21-5 1,4-dibenzyloxybut-2-yne 
• 564-00-1 meso-1,2,3,4-diepoxybutane 

Downstream Products

• 17137-53-0 Methanesulfonic acid (1R,2S)-3-benzyloxy-1-benzyloxymethyl-2-methanesulfonyloxy-propyl ester 
• 195374-95-9 (2S,4R,5S)-4,5-Bis-benzyloxymethyl-2-phenylethynyl-[1,3]dioxolane 
• 1262957-89-0 C₁₉H₂₀O₂S 
• 1298086-41-5 (R)-1,4-bis(benzyloxy)-3-hydroxybutan-2-one 
• 1507365-42-5 (S)-1,4-bis(benzyloxy)-3-hydroxybutan-2-one 
• 71806-86-5 (4R,5S)-4,5-bis((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolane 
• 88454-94-8 C₃₆H₅₄O₁₀ 
• 17401-06-8 (2S,3S)-1,4-bis(benzyloxy)-2,3-butanediol 
• 91604-41-0 (R,R)-1,4-dibenzylthreitol 

Relevant academic research and scientific papers

A lipase-mediated synthesis of single enantiomeric trans-epoxides via convergence of racemic mixtures

A new lipase-mediated methodology has been devised for the preparation of single enantiomeric trans-epoxides from unsymmetrical cis-olefin precursors via enantiomeric convergence of racemic intermediates.

Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts

An extremely efficient acylative kinetic resolution of d,l-1,2-diols in the presence of only 0.5 mol% of binaphthyl-based chiral N,N-4-dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert-alcohol unit(s) of the catalyst and the 1,2-diol unit of the substrate is critical for accelerating the rate of monoacylation and achieving high enantioselectivity. This catalytic system can be applied to a wide range of substrates involving racemic acyclic and cyclic 1,2-diols with high selectivity factors. The kinetic resolution of d,l-hydrobenzoin and trans-1,2-cyclohexanediol on a multigram scale (10 g) also proceeded with high selectivity and under moderate reaction conditions: (i) very low catalyst loading (0.1 mol%); (ii) an easily achievable low reaction temperature (0 °C); (iii) high substrate concentration (1.0 M); and (iv) short reaction time (30 min). (Figure presented.).

Desymmetrization of meso-1,2-Diols by a Chiral N,N-4-Dimethylaminopyridine Derivative Containing a 1,1′-Binaphthyl Unit: Importance of the Hydroxy Groups

We developed an acylative desymmetrization of meso-1,2-diols using a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1h with tert-alcohol substituents. The reaction proceeds with a wide range of acyclic meso-1,2-diols and six-membered-ring meso-1,2-diols to provide a monoacylate selectively with a high enantiomeric ratio (er). Only 0.1 mol % of the catalyst facilitated the reaction within a short reaction time (3 h) to afford enantio-enriched monoacylated products in moderate to good yield. Several control experiments revealed that the tert-alcohol units of catalyst 1h play a significant role in achieving high catalytic activity, chemoselectivity of monoacylation, and enantioselectivity.

Total Synthesis of Ovafolinins A and B: Unique Polycyclic Benzoxepin Lignans through a Cascade Cyclization

Ovafolinins A and B, isolated from Lyonia ovalifolia var. elliptica, are lignans that contain a unique bridged structure containing a penta- and tetracyclic benzoxepin and an aryl tetralin. We report the first total synthesis of these natural products in which an acyl-Claisen rearrangement was initially utilized to construct the lignan backbone with correct relative stereochemistry. Judicious use of a bulky protecting group placed reactive moieties in the correct orientation, thereby resulting in a cascade reaction to form the bridged benzoxepin/aryl tetralin from a linear precursor in a single step. Modification of this route allowed the enantioselective synthesis of (+)-ovafolinins A and B, which confirmed the absolute stereochemistry, and comparison of optical rotation suggests that these compounds are found as scalemic mixtures in nature.

Total synthesis of (-)-bicubebin A, B, (+)-bicubebin C and structural reassignment of (-)-cis-cubebin

The first total synthesis of (-)-bicubebin A, and two previously unreported dilignans, (-)-bicubebin B and (+)-bicubebin C has been achieved through the dimerization of (-)-cubebin, confirming the structure and absolute stereochemistry of (-)-bicubebin A. Analysis of the data for (-)-bicubebin B showed it matched that of reported compound (-)-cis-cubebin. The NMR data of the subsequently synthesized proposed structure of cis-cubebin confirmed that its original proposed structure was incorrect.

Enantioselective oxidation of 1,2-diols with quinine-derived urea organocatalyst

Quinine-derived urea has been identified as a highly efficient organocatalyst for the enantioselective oxidation of 1,2-diols using bromination reagents as the oxidant. This simple procedure utilizes readily available reagents and operates at ambient temperature to yield a wide range of α-hydroxy ketones in good yield (up to 94%) and excellent enantioselectivity (up to 95% ee).

Synthesis of thietane nucleoside with an anomeric hydroxymethyl group

Thietane nucleoside 5 with an anomeric hydroxymethyl group was synthesized via the Pummerer reaction. The stereochemistry of the sulfoxide and the nature of the protecting group had no significant effect on the yield of the reaction. When a hypervalent iodine reagent was used, sulfide 16 with O-benzoyl protecting groups gave the ring-expanded nucleoside 21. Unfortunately, synthesized compound 6 did not exhibit anti-HSV activity. Copyright

Rhutenium-Catalyzed cis-Dihydroxylation of Alkenes: Scope and Limitations

Oxidative ruthenium catalysis (0.07 molequiv RuCl3*(H2O)3, 1.5 molequiv NaIO4, EtOAc/CH3CN/H2O 3:3:1), beyond the usual C-C bond cleavage to give dicarbonyls, have been shown to syn-dihydroxylate a wide range of alkenes (except for strained bicyclic alkenes, sterically hindered trisubstituted alkenes, and most tetrasubstituted alkenes) to give vicinal diols rapidly (within minutes) and efficiently.The minor products are the usual oxidative fission products, namely, ketones and aldehydes or carboxylic acids, and sometimes ketols.Longer reaction times lower the yields of most diols, probably owing to oxidative glycol cleavage.Reactions with substrates containing one or more electron-withdrawing groups in conjugation with or adjacent to the alkene moiety are generally slower but give better yields.The diastereoselectivity of the present "flash" dihydroxylation, anti to the existing α-stereogenic center, with cycloalkenes is excellent whereas that with acyclic alkenes is moderate to poor.Sodium metaperiodate is still the best co-oxidant for the catalytic reaction.Aqueous acetonitrile (approximately 86percent) as an alternative solvent system was found to give better yields of 1,2-diols than the original solvent system in some cases. - Keywords: alkenes, catalysis, dihydroxylations, electrophilicity, ruthenium compounds.