192047-48-6

Upstream product

• 95452-06-5 tert-butyl(1,3-dithian-2-yl)dimethylsilane 
• 14618-80-5 (R)-benzyl glycidol 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 392230-13-6 (2R)-1-benzyloxy-3-[1,3]dithian-2-yl-propan-2-ol 
• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 192047-43-1 (2R)-1-benzyloxy-3-{2-[(2R)-3-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-[1,3]dithian-2-yl}-propan-2-ol 
• 392230-23-8 (2R,6R)-1,7-Bis-benzyloxy-2,6-bis-(tert-butyl-dimethyl-silanyloxy)-heptan-4-one 
• 392230-14-7 2,2-bis-[(2R,2R)-3-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-[1,3]dithiane 
• 392230-15-8 (2R,6R)-1,7-bis-benzyloxy-2,4,6-tris-(tert-butyl-dimethyl-silanyloxy)-heptane 

Relevant academic research and scientific papers

Multicomponent Linchpin Couplings. Reaction of Dithiane Anions with Terminal Epoxides, Epichlorohydrin, and Vinyl Epoxides: Efficient, Rapid, and Stereocontrolled Assembly of Advanced Fragments for Complex Molecule Synthesis

The development, application, and advantages of a one-flask multicomponent dithiane linchpin coupling protocol, over the more conventional stepwise addition of dithiane anions to electrophiles leading to the rapid, efficient, and stereocontrolled assembly of highly functionalized intermediates for complex molecule synthesis, are described. Competent electrophiles include terminal epoxides, epichlorohydrin, and vinyl epoxides. High chemoselectivity can be achieved with epichlorohydrin and vinyl epoxides. For vinyl epoxides, the steric nature of the dithiane anion is critical; sterically unencumbered dithiane anions afford SN2 adducts, whereas encumbered anions lead primarily to SN2′ adducts. Mechanistic studies demonstrate that the SN2′ process occurs via syn addition to the vinyl epoxide. Integration of the multicomponent tactic with epichlorohydrin and vinyl epoxides permits the higher-order union of four and five components.

Diastereoselective synthesis of 2,3,5-trisubstituted tetrahydrofurans via cyclofunctionalization reactions. Evidence of stereoelectronic effects

The work described herein considers the impact of stereoelectronic effects and allylic 1,3-strain in controlling the cyclofunctionalization reaction when a hydroxyl group is at the allylic position. The stereoelectronic arguments are supported by independent iodocyclization reactions performed using two secondary alcohols. The transition-state pathways involved in these reactions are established through a comparison of relative reaction rates. A bi-directional approach is used to demonstrate the potential of the iodocyclization reaction to differentiate a terminus in molecules with a pseudo C2 axis of symmetry, showing that two-directional synthesis can be used to differentiate between alternative transition-state pathways.