334792-03-9

Upstream product

• 334784-76-8 (2S,3S,4R)-3-benzyloxy-2-iodomethyltetrahydrofuran-4-ol 
• 862972-77-8 (2R,3RS)-3-O-benzyl-4-pentene-1,2,3-triol 
• 243970-88-9 1,4-anhydro-3,5-di-O-benzyl-D-xylitol 
• 220788-30-7 (2R,3R)-1,3-di-O-benzyl-4-pentene-1,2,3-triol 
• 115483-04-0 (2R,3R)-3-O-benzyl-4-pentene-1,2,3-triol 
• 108341-87-3 (2R,3R)-3-O-benzyl-1,2-O-isopropylidene-4-pentene-1,2,3-triol 
• 100-39-0 benzyl bromide 
• 212579-64-1 (4R)-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)allyl alcohol 

Downstream Products

• 334784-71-3 (2S,3R,4R)-3-benzyloxy-2-iodomethyltetrahydrofuran-4-ol 
• 334784-76-8 (2S,3S,4R)-3-benzyloxy-2-iodomethyltetrahydrofuran-4-ol 

Relevant academic research and scientific papers

Palladium-catalysed cyclisation of alkenols: Synthesis of oxaheterocycles as core intermediates of natural compounds

The study of Pd-catalysed cyclisation reactions of alkenols using different catalytic systems is reported. These transformations affect the stereoselective construction of mono- and/or bicyclic oxaheterocyclic derivatives depending on a starting alkenol. The substrate scope and proposed mechanism of Pd-catalysed cyclisation reactions are also discussed. Moreover, the diastereoselectivePd-catalysed cyclisation of appropriate alkenols to tetrahydrofurans and subsequent cyclisation provided properly substituted 2,5-dioxabicyclo[2.2.1]heptane and 2,6-dioxabicyclo[3.2.1]octane, respectively. Such bicyclic ring subunits are found in many natural products including ocellenynes and aurovertines.

Allyloxy and propargyloxy group migration: Role of remote group participation in the synthesis of 5-C-nucleosides and other sugar derivatives

In 1-deoxy-xylofuranose derivatives possessing a good leaving group at 2-C, participation of allyloxy and propargyloxy substituents at 5-C results in loss of the 2-C substituent and attack of various nucleophiles at 5-C of the oxonium intermediate. Such p

Novel bicyclisation of unsaturated polyols in PdCl2-CuCl 2-AcOH catalytic system

Novel type of Pd(II)-catalysed transformation of sugar-derived alkenitols furnishing 7-benzyloxy-2,5-dioxabicyclo[2.2.1]heptanes was discovered. The investigated bicyclisation displays an exceptional substrate selectivity towards xylo-configured unsaturat

Synthesis of tetrahydrofurans through a novel pseudo-meso-trick

Diastereoselective synthesis of trisubstituted tetrahydrofuran (D-lyxo-4) from the equimolar diastereomeric mixture of D-erythro-/D-threo-1-pentenitols (1) is described. The synthesis exploits a sequence of two novel reactions: diastereospecific palladium

Synthesis of substituted tetrahydrofuran by electrophile-induced cyclization of 4-pentene-1,2,3-triols - An example of 5-exo versus 5-endo cyclization governed by the electrophile

Differently protected 4-pentene-1,2,3-triols 5-8 were obtained from glyceraldehyde and submitted to iodine-based electrophile-induced cyclization to give tetrahydrofuran derivatives 10 and 18, with high chemo-, regio-, and stereo-selectivity, through a 5-exo cyclization process. However, when an electrophilic selenium reagent was treated with similar alkene triols 5, 7, and 8, the product depended on the protecting group at the primary hydroxy moiety. Thus, while compounds 5a and 5b, unprotected at the primary hydroxy group, give compounds 26 and 27, and 32 and 33, respectively, through a 5-exo cyclization process, compounds 7 and 8, protected at the primary hydroxy group, give the 5-endo cyclization products 22-25 and 28-31 in good yields. The electrophile-induced cyclization of 4-pentene-1,2,3-triols to give tetrahydrofuran derivatives can be directed towards a 5-exo process by the use of iodine or, when the primary hydroxy group is unprotected, selenium. When the primary hydroxy group is protected, use of selenium results in 5-endo cyclization.